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Methoxycarbonyl-L-tert-leucine

Description References
Product Name
Methoxycarbonyl-L-tert-leucine
CAS No.
162537-11-3
Chemical Name
Methoxycarbonyl-L-tert-leucine
Synonyms
(S)-2-acetamido-3,3-dimethylbutanoic acid;MOC-L-tert.Leucine;N-Methoxycarbonyl-tert-leucine;(S)-2-(MethoxycarbonylaMino)-3,3-diMethylbutanoic acid;Moc-L-tle;Moc-Tle-OH;MOC-L-Norleucine;Moc-L-tert-lecine;MOC-L-tert. Leucin;Atazanavir USP RC A
CBNumber
CB6663762
Molecular Formula
C8H15NO4
Formula Weight
189.21
MOL File
162537-11-3.mol
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Methoxycarbonyl-L-tert-leucine Property

Melting point:
1090C
Boiling point:
320.9±25.0 °C(Predicted)
Density 
1.126±0.06 g/cm3(Predicted)
vapor pressure 
0Pa at 25℃
storage temp. 
2-8°C
solubility 
Soluble in ethyl acetate and methanol.
pka
4.46±0.10(Predicted)
form 
powder
color 
White to off-white
Water Solubility 
26.4g/L at 20℃
InChI
InChI=1S/C8H15NO4/c1-8(2,3)5(6(10)11)9-7(12)13-4/h5H,1-4H3,(H,9,12)(H,10,11)/t5-/m1/s1
InChIKey
NWPRXAIYBULIEI-RXMQYKEDSA-N
SMILES
C(O)(=O)[C@H](C(C)(C)C)NC(OC)=O
LogP
0.832 at 21℃
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Safety

HS Code 
2933399090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR3001
Product name
Atazanavir Related Compound A
Purity
pharmaceutical secondary standard, certified reference material
Packaging
50MG
Price
$433
Updated
2025/07/31
Sigma-Aldrich
Product number
1044356
Product name
Atazanavir Related Compound A
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
25mg
Price
$1200
Updated
2025/07/31
Usbiological
Product number
281876
Product name
Methoxycarbonyl-L-tert-leucine
Packaging
50g
Price
$342
Updated
2021/12/16
TRC
Product number
M261295
Product name
N-(Methoxycarbonyl)-L-tert-leucine
Packaging
5g
Price
$955
Updated
2021/12/16
AK Scientific
Product number
J91104
Product name
(S)-N-(Methoxycarbonyl)-tert-leucine
Packaging
5g
Price
$23
Updated
2021/12/16
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Methoxycarbonyl-L-tert-leucine Chemical Properties,Usage,Production

Description

Methoxycarbonyl-L-tert-leucine is a kind of amino acid deriviative. It is a very useful intermediate for efficient synthesis of the HIV protease inhibitor BMS-232632 as well as atazanavir bisulfate. 

References

Zhongmin Xu, †, et al. "Process Research and Development for an Efficient Synthesis of the HIV Protease Inhibitor BMS-232632." Organic Process Research & Development 6.3(2002):323-328.
Simhadri, Srinivas. "Process for the preparation of atazanavir bisulfate." (2016).
https://www.alfa.com/en/search/?q=14328-63-3

Chemical Properties

White Solid

Uses

The coupling of the two key intermediates, N-(methoxycarbonyl)-l-tert-leucine acylated benzyl hydrazine and chloromethyl ketone, via an S N 2 reaction furnished the amino ketone in high yield under our optimized conditions in practical synthesis of the HIV Protease Inhibitor Atazanavir via a Highly diastereoselective Reduction Approach.

Flammability and Explosibility

Not classified

Synthesis

20859-02-3

79-22-1

162537-11-3

Step 1: Synthesis of (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid: (S)-2-amino-3,3-dimethylbutanoic acid (5.0 g, 38.6 mmol) was dissolved in a mixture of dioxane (20 ml) and 2N sodium hydroxide solution (62 ml, pH=8-9) at 0 °C. Methyl chloroformate (5.88 ml, 76.33 mmol) was added dropwise with stirring. The reaction mixture was warmed up to 60°C with continuous stirring for 18 hours. After completion of the reaction, the mixture was cooled to room temperature and extracted with dichloromethane (DCM) to separate the aqueous layer. The aqueous layer was acidified to acidity with 1N hydrochloric acid and then extracted with ethyl acetate (EtOAc). The organic layer was dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to remove the solvent. The resulting crude product was stirred and distilled in hexane to give N-methoxycarbonyl-L-tert-leucine as a white solid. Yield: 8.5 g (quantitative yield). NMR hydrogen spectrum (300MHz, CDCl3): δ5.25 (d, 1H, J=10.5Hz), 4.19 (d, 1H, J=9.6Hz), 3.70 (s, 3H), 1.03 (s, 9H). Mass spectrum: [M-1]- 188 (100%). IR spectrum (potassium bromide pressed, cm-1): 3379, 2974, 1727, 1688, 1546, 1466, 1332, 1263, 1211, 1070, 1034, 1018, 843, 696.

References

[1] Patent: WO2011/80562, 2011, A1. Location in patent: Page/Page column 34
[2] Patent: WO2005/61487, 2005, A1. Location in patent: Page/Page column 109
[3] Patent: US2005/159469, 2005, A1. Location in patent: Page/Page column 56
[4] Patent: EP2423187, 2012, A1. Location in patent: Page/Page column 11
[5] Patent: US2005/131017, 2005, A1. Location in patent: Page/Page column 95

Methoxycarbonyl-L-tert-leucine Preparation Products And Raw materials

Raw materials

Preparation Products

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Methoxycarbonyl-L-tert-leucine Suppliers

Canada 2 China 374 Germany 6 India 35 Russia 1 Switzerland 1 The Netherlands 1 United Kingdom 5 United States 28 Global 453
Karl H. Boddin Chemiehandel GmbH
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Germany
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ABCR GmbH & CO. KG
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Germany
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6831
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Evonik Industries AG.
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Germany
ProdList
351
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Alfa Aesar, Thermo Fisher Scientific
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es@alfa.com
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Germany
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5123
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CHEMOS GmbH & Co. KG
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chemos@chemos.de
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Germany
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6727
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Service Chemical Inc.
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sales@chemos-group.com
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Germany
ProdList
6350
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View Lastest Price from Methoxycarbonyl-L-tert-leucine manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Methoxycarbonyl-L-tert-leucine 162537-11-3
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
99%min
Supply Ability
1000kg
Release date
2021-08-28
Henan Aochuang Chemical Co.,Ltd.
Product
Methoxycarbonyl-L-tert-leucine 162537-11-3
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1ton
Release date
2022-09-28
Shanghai Joiny Pharmaceutical Co.,LTD
Product
N-Methoxycarbonyl-L-tert-Leucine 162537-11-3
Price
US $0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20tons
Release date
2022-02-21

162537-11-3, Methoxycarbonyl-L-tert-leucineRelated Search:

Stearic acid tert-Butyl peroxyacetate N-CARBOBENZOXY-DL-LEUCINE tert-Butanol L-tert-Leucine Folic acid METHOXYCARBONYLSULFENYL CHLORIDE Ethyl 2-(Chlorosulfonyl)acetate Citric acid DL-Leucine Ascoric Acid Fmoc-L-tert-leucine (S)-N-Boc-3,3-dimethylpyrrolidine-2-carboxylic acid Cbz-L-tert-Leucine (2S,4R)-N-Boc-4-hydroxy-3,3-dimethylpyrrolidine-2-carboxylic acid Z-TLE-OH DCHA N-(METHOXYCARBONYL)-L-TERT-LEUCINE FMOC-D-ALPHA-T-BUTYLGLYCINE

  • MOC-L-tert.Leucine
  • (S)-2-Methoxycarbonylamino-3,3-dimethylbutyric acid
  • Methoxycarbonyl-L-tert-leucine
  • N-(Methoxycarbonyl)-3-methyl-L-valine
  • N-Methoxycarbonyl-tert-leucine
  • Atazanavir related coMpound A
  • MOC-L-tert. Leucin
  • L-Valine,N-(Methoxycarbonyl)-3-Methyl-
  • (S)-2-(MethoxycarbonylaMino)-3,3-diMethylbutanoic acid
  • Moc-L-tert-lecine
  • (S)-2-(Methoxycarbonyl)-3,3-diMethylbutanoic acid
  • Methyl Carbonyl L-tert Leucine
  • (2S)-2-ACETAMIDO-3,3-DIMETHYLBUTANOIC ACID
  • N-Moc-L-tert-Leucine
  • (S)-2-acetamido-3,3-dimethylbutanoic acid
  • Atazanavir USP Related Compound A
  • (S)-N-(METHOXYCARBONYL)-TERT-LEUCINE
  • Methylcarbonyl-L-t-Leucine
  • Methoxycarbonyl-L-tert-leucinef
  • Atazanavir side chain
  • Atazanavir Impurity 15
  • Atazanavir USP RC A
  • N-Methoxycarbonyl-L-tert-leucine,98%
  • Methoxycarbonyl-L-tert-leucine USP/EP/BP
  • Moc-Tle-OH
  • Atazanavir Related Compund A (Methoxycarbonyl-L-tert-leucine)
  • Atazanavir Related Compound A ((S)-2-[(Methoxycarbonyl)amino]-3,3-dimethylbutanoic acid) (1044356)
  • MOC-L-Norleucine
  • Atazanavir Sulfate EP Impurity K
  • Moc-L-tle
  • N-(Methoxycarbonyl)-tert-L-leucine
  • Azanavir EP Impurity K
  • Atazanavir Sulfate Impurity K
  • N-Methoxycarbonyl-L-Tert-Leucine (MOC-L-T-Leu)
  • 162537-11-3
  • C38H54N6O11S
  • Amino Acid Derivatives
  • Amino Acids 13C, 2H, 15N
  • Amino Acids & Derivatives
  • Chiral Reagents