ChemicalBook > CAS DataBase List > (1S-4R)-4-[[(1,1-diMethylethoxy)carbonyl]aMino]- 2-Cyclopentene-1-carboxylic acid Methyl ester

(1S-4R)-4-[[(1,1-diMethylethoxy)carbonyl]aMino]- 2-Cyclopentene-1-carboxylic acid Methyl ester

Product Name
(1S-4R)-4-[[(1,1-diMethylethoxy)carbonyl]aMino]- 2-Cyclopentene-1-carboxylic acid Methyl ester
CAS No.
229613-93-8
Chemical Name
(1S-4R)-4-[[(1,1-diMethylethoxy)carbonyl]aMino]- 2-Cyclopentene-1-carboxylic acid Methyl ester
Synonyms
methyl (3aR,4R,6S,6aS)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-3-pentan-3-yl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,2]oxazole-6-carboxylate;(1S-4R)-4-[[(1;Peramivir impurities5;Peramivir Impurity N1;Peramivir impurities 7;Peramivir Intermediate 2;Peramivir intermediate M8;6aS)-Methyl 4-(tert-butoxycarbonyl)-3-(pentan-3-yl)-4;6a-tetrahydro-3aH-cyclopenta[d]isoxazole-6-carboxylate;(1S,4R)-4-[[(1,1-diMethylethoxy)carbonyl]amino]- 2-Cyclopent...
CBNumber
CB82553360
Molecular Formula
C18H30N2O5
Formula Weight
354.44
MOL File
229613-93-8.mol
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(1S-4R)-4-[[(1,1-diMethylethoxy)carbonyl]aMino]- 2-Cyclopentene-1-carboxylic acid Methyl ester Property

Melting point:
67-69°C
Density 
1.22±0.1 g/cm3(Predicted)
storage temp. 
Sealed in dry,Room Temperature
solubility 
Chloroform (Sparingly), Methanol (Slightly)
pka
11.61±0.60(Predicted)
form 
Solid
color 
Off-White to Pale Beige
InChI
InChI=1S/C18H30N2O5/c1-7-10(8-2)14-13-12(19-17(22)24-18(3,4)5)9-11(16(21)23-6)15(13)25-20-14/h10-13,15H,7-9H2,1-6H3,(H,19,22)/t11-,12+,13+,15+/m0/s1
InChIKey
WYUYCGDXMIJIAZ-KYEXWDHISA-N
SMILES
O1[C@]2([H])[C@@H](C(OC)=O)C[C@@H](NC(OC(C)(C)C)=O)[C@]2([H])C(C(CC)CC)=N1
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC
Product number
D472890
Product name
(3aR,4R,6S,6aS)-4-[[(1,1-Dimethylethoxy)carbonyl]amino]-3-(1-ethylpropyl)-3a,5,6,6a-tetrahydro-4H-cyclopent[d]isoxazole-6-carboxylicAcidMethylEster
Packaging
1g
Price
$110
Updated
2021/12/16
AK Scientific
Product number
8197CR
Product name
CID10522092
Packaging
1g
Price
$73
Updated
2021/12/16
Medical Isotopes, Inc.
Product number
64529
Product name
(3aR,4R,6S,6aS)-4-[[(1,1-Dimethylethoxy)carbonyl]amino]-3-(1-ethylpropyl)-3a,5,6,6a-tetrahydro-4H-cyclopent[d]isoxazole-6-carboxylicAcidMethylEster
Packaging
1g
Price
$610
Updated
2021/12/16
Ambeed
Product number
A180683
Product name
(3aR,4R,6S,6aS)-Methyl4-((tert-butoxycarbonyl)amino)-3-(pentan-3-yl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-6-carboxylate
Purity
95%
Packaging
1g
Price
$10
Updated
2021/12/16
Ambeed
Product number
A180683
Product name
(3aR,4R,6S,6aS)-Methyl4-((tert-butoxycarbonyl)amino)-3-(pentan-3-yl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-6-carboxylate
Purity
95%
Packaging
5g
Price
$31
Updated
2021/12/16
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(1S-4R)-4-[[(1,1-diMethylethoxy)carbonyl]aMino]- 2-Cyclopentene-1-carboxylic acid Methyl ester Chemical Properties,Usage,Production

Uses

(3aR,4R,6S,6aS)-4-[[(1,1-Dimethylethoxy)carbonyl]amino]-3-(1-ethylpropyl)-3a,5,6,6a-tetrahydro-4H-cyclopent[d]isoxazole-6-carboxylic Acid Methyl Ester is an intermediate used in the synthesis of peramivir (P285500), a neuraminidase inhibitor developed as an antiviral agent for the treatment of influenza.

Synthesis

316173-28-1

77-78-1

229613-93-8

1. (3aR,4R,6S,6aS)-4-((tert-butoxycarbonyl)amino)-3-(pentan-3-yl)-3a,5,6,6a-tetrahydro-4H-cyclopenta[d]isoxazole-6-carboxylic acid 2-methylpropan-2-ammonium salt (3210 g, 7.8 mol) was suspended in acetone (4000 g). 2. potassium carbonate (53.8 g) and 30% aqueous sodium hydroxide (containing 312 g sodium hydroxide) were added to the suspension. 3. 3000 ml of solvent was removed by evaporation, 3000 ml of acetone was added and 3000 ml of solvent was again removed by evaporation. This operation was repeated once, and finally 4000 ml of acetone was removed by evaporation to obtain a reaction solution essentially free of tert-butylamine odor. 4. Cool the reaction solution to 30-35°C and slowly add 1060 ml of dimethyl sulfate dropwise, controlling the rate of dropwise acceleration in order to keep the reaction temperature from exceeding 45°C. After the dropwise acceleration is completed, the reaction solution is added to the reaction solution. 5. After the dropwise addition, the reaction mixture was stirred at 40-45°C for 1.5 hours. 6. The reaction mixture was cooled to 15-20 °C, 1500 ml of 25% ammonia was added and stirred for 30 minutes. 7. After addition of 1500 ml of methanol, the reaction mixture was cooled to 0-5 °C. 8. 2240 ml of 25% ammonia was slowly added to the reaction mixture over 45 minutes. 9. The product was collected by filtration, washed with 3000 ml of water and dried under vacuum at 45-50 °C. 10. 2686.2 g of the target product was finally obtained in 97.13% yield.

References

[1] Patent: EP2186795, 2010, A1. Location in patent: Page/Page column 6; 11-12

(1S-4R)-4-[[(1,1-diMethylethoxy)carbonyl]aMino]- 2-Cyclopentene-1-carboxylic acid Methyl ester Preparation Products And Raw materials

Raw materials

Preparation Products

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(1S-4R)-4-[[(1,1-diMethylethoxy)carbonyl]aMino]- 2-Cyclopentene-1-carboxylic acid Methyl ester Suppliers

China 216 India 4 United States 6 Global 226
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View Lastest Price from (1S-4R)-4-[[(1,1-diMethylethoxy)carbonyl]aMino]- 2-Cyclopentene-1-carboxylic acid Methyl ester manufacturers

Jinan Jianfeng Chemical Co., Ltd
Product
(1S-4R)-4-[[(1,1-diMethylethoxy)carbonyl]aMino]- 2-Cyclopentene-1-carboxylic acid Methyl ester 229613-93-8
Price
US $0.00/kg
Min. Order
1kg
Purity
99%min
Supply Ability
20ton
Release date
2024-08-09
Jinan Jianfeng Chemical Co., Ltd
Product
(1S-4R)-4-[[(1,1-diMethylethoxy)carbonyl]aMino]- 2-Cyclopentene-1-carboxylic acid Methyl ester 229613-93-8
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99%min
Supply Ability
20ton
Release date
2024-08-09
Henan Aochuang Chemical Co.,Ltd.
Product
(1S-4R)-4-[[(1,1-diMethylethoxy)carbonyl]aMino]- 2-Cyclopentene-1-carboxylic acid Methyl ester 229613-93-8
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
1Ton
Release date
2022-09-30

229613-93-8, (1S-4R)-4-[[(1,1-diMethylethoxy)carbonyl]aMino]- 2-Cyclopentene-1-carboxylic acid Methyl esterRelated Search:

Peramivir Impurity 1 (2S)-2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-1-Pyrrolidinecarboxylic acid phenylmethyl ester Peramivir methyl (3aS,4R,6S,6aR)-4-((tert-butoxycarbonyl)amino)-3-(pentan-3-yl)-3a,5,6,6a-tetrahydro-4H-cyclopenta[d]isoxazole-6-carboxylate Peramivir Peramivir Peramivir Impurity 70 Peramivir Impurity 58 Peramivir Impurity 36 Peramivir Impurity 31 Peramivir Impurity 20 Peramivir Impurity 16 Peramivir Impurity 9 Peramivir Impurity 4 Peramivir Impurity 78 Peramivir Impurity 51 Peramivir Impurity 45 Peramivir Impurity 43

  • Peramivir Intermediate 2
  • methyl 2-((1R,4R)-4-((tert-butoxycarbonyl)amino)cyclopent-2-en-1-yl)acetate
  • (1S-4R)-4-[[(1,1-diMethylethoxy)carbonyl]aMino]- 2-Cyclopentene-1-carboxylic acid Methyl ester
  • Methyl 4-{[(tert-butoxy)carbonyl]aMino}-3-(pentan-3-yl)-3aH,4H,5H,6H,6aH-cyclopenta[d][1,2]oxazole-6-carboxylate
  • (3aR,4R,6S,6aS)-4-[[(1,1-Dimethylethoxy)carbonyl]amino]-3-(1-ethylpropyl)-3a,5,6,6a-tetrahydro-4H-cy
  • (3aR,4R,6S)-Methyl-4-((tert-butoxycarbonyl)aMino)-3-(pentan-3-yl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-6-carboxylate
  • (3aR,4R,6S,6aS)-Methyl 4-(tert-butoxycarbonyl)-3-(pentan-3-yl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-6-carboxylate
  • (3aR,4R,6S,6aS)-4-[[(1,1-DiMethylethoxy)carbonyl]aMino]-3-(1-ethylpropyl)-3a,5,6,6a-tetrahydro-4H-cyclopent[d]isoxazole-6-carboxylic Acid Methyl Ester
  • methyl (3aR,4R,6S,6aS)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-3-pentan-3-yl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,2]oxazole-6-carboxylate
  • (1S-4R)-4-[[(1
  • 1-diMethylethoxy)carbonyl]aMino]- 2-Cyclopentene-1-carboxylic acid Methyl ester
  • methyl (3aS,4S,6R,6aR)-4-((tert-butoxycarbonyl)amino)-3-(pentan-3-yl)-3a,5,6,6a-tetrahydro-4H-cyclopenta[d]isoxazole-6-carboxylate
  • 4H-Cyclopent[d]isoxazole-6-carboxylic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-(1-ethylpropyl)-3a,5,6,6a-tetrahydro-, methyl ester, (3aR,4R,6S,6aS)-
  • (1S,4R)-4-[[(1,1-diMethylethoxy)carbonyl]amino]- 2-Cyclopent...
  • Peramivir impurities5
  • TIANFU-CHEM--(1S-4R)-4-[[(1,1-diMethylethoxy)carbonyl]aMino]- 2-Cyclopentene-1-carboxylic acid Methyl ester
  • Peramivir impurities 7
  • Peramivir intermediate M8
  • methyl (3aR,4R,6S,6aS)-4-((tert-butoxycarbonyl)amino)-3-(pentan-3-yl)-3a,5,6,6a-tetrahydro-4H-cyclopenta[d]isoxazole-6-carboxylate
  • (3R.AR.6S6aS)-Methry1 4-tetebutotocroo--(an-an-3-45.6.a.tatrahcyro-3aHarcloentatdjisoxazol-caoxyatea
  • methyl (3aR,6aS)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-3-pentan-3-yl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,2]oxazole-6-carboxylate
  • Peramivir Impurity N1
  • 6aS)-Methyl 4-(tert-butoxycarbonyl)-3-(pentan-3-yl)-4
  • 6a-tetrahydro-3aH-cyclopenta[d]isoxazole-6-carboxylate
  • methyl(3aR,4R,6S,6aS)-4-((tert-butoxycarbonyl)amino)-3-(pentan-3-yl)-3a,5,6,6a-tetrahydro-4H-cyclopenta[d]isoxazole-6-carboxylate3
  • 229613-93-8
  • C18H30N2O5
  • 229613-93-8