ChemicalBook > CAS DataBase List > N-Boc-trans-4-Hydroxy-L-proline methyl ester

N-Boc-trans-4-Hydroxy-L-proline methyl ester

Product Name
N-Boc-trans-4-Hydroxy-L-proline methyl ester
CAS No.
74844-91-0
Chemical Name
N-Boc-trans-4-Hydroxy-L-proline methyl ester
Synonyms
1-tert-Butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate;BOC-HYP-OME;Boc-L-Hyp-OMe;N-BOC-4-HYDROXY-L-PROLINE METHYL ESTER;1-tert-butyl 2-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate;GOSO-001;BoC-Hyp-0me;BOC-L-Hyp Methyl ester;BOC-HYDROXYPROLINE-OME;N-Boc-trans-4-hydroxy-L
CBNumber
CB2207339
Molecular Formula
C11H19NO5
Formula Weight
245.27
MOL File
74844-91-0.mol
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N-Boc-trans-4-Hydroxy-L-proline methyl ester Property

Melting point:
92-96 °C (lit.)
alpha 
-65 º (c=1 CHCl3)
Boiling point:
132°C/0.05mmHg(lit.)
Density 
1.216±0.06 g/cm3(Predicted)
storage temp. 
Keep in dark place,Sealed in dry,Room Temperature
solubility 
Soluble in chloroform, dichloromethane and ethyl acetate.
form 
Crystalline Powder
pka
14.27±0.40(Predicted)
color 
White to light beige
optical activity
[α]20/D -65°, c = 1% in chloroform
InChI
InChI=1S/C11H19NO5/c1-11(2,3)17-10(15)12-6-7(13)5-8(12)9(14)16-4/h7-8,13H,5-6H2,1-4H3/t7-,8+/m1/s1
InChIKey
MZMNEDXVUJLQAF-SFYZADRCSA-N
SMILES
N1(C(OC(C)(C)C)=O)C[C@H](O)C[C@H]1C(OC)=O
LogP
0.813 at 25℃
CAS DataBase Reference
74844-91-0(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn
Risk Statements 
20/21/22-36/37/38
Safety Statements 
24/25-36-26
WGK Germany 
3
HazardClass 
IRRITANT
HS Code 
29339900
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

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

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
639737
Product name
N-Boc-trans-4-hydroxy-L-proline methyl ester
Purity
97%
Packaging
5g
Price
$21.36
Updated
2025/07/31
TCI Chemical
Product number
B3843
Product name
N-(tert-Butoxycarbonyl)-trans-4-hydroxy-L-proline Methyl Ester
Purity
>95.0%(GC)
Packaging
1g
Price
$30
Updated
2025/07/31
TCI Chemical
Product number
B3843
Product name
N-(tert-Butoxycarbonyl)-trans-4-hydroxy-L-proline Methyl Ester
Purity
>95.0%(GC)
Packaging
5g
Price
$87
Updated
2025/07/31
TRC
Product number
H656560
Product name
(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylicAcid1-tert-ButylEster2-MethylEster
Packaging
250g
Price
$485
Updated
2021/12/16
Apolloscientific
Product number
OR43520
Product name
1-tert-Butyl2-methyl(2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate
Packaging
500g
Price
$508
Updated
2021/12/16
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N-Boc-trans-4-Hydroxy-L-proline methyl ester Chemical Properties,Usage,Production

Chemical Properties

Clear Colourless Oil

Uses

A potential iNOS inhibitor.

Uses

It is used in the synthesis of For-Met-Leu-Phe-OMe (fMLF-OMe) analogues based on Met residue replacement by 4-amino-proline scaffold.

Uses

(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic Acid 1-tert-Butyl Ester 2-Methyl Ester roline scaffold.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

24424-99-5

40216-83-9

74844-91-0

The general procedure for the synthesis of N-Boc-trans-4-hydroxy-L-proline methyl ester from di-tert-butyl dicarbonate and trans-4-hydroxy-L-proline methyl ester hydrochloride was as follows: the trans-4-hydroxy-L-proline methyl ester hydrochloride (14.5 g, 0.1 mol) obtained in step I was suspended in CH2Cl2 (400 mL), cooled to 0 °C, and with stirring, sequentially Et3N (28 mL, 0.2 mol), DMAP (0.61 g, 5 mmol) and Boc anhydride (27.5 mL, 0.12 mol) were added. The reaction mixture was gradually warmed to room temperature and stirring was continued for 2 hours. After completion of the reaction, the solvent was removed by concentration under reduced pressure, ether was added to the residual solid, the solid was collected by filtration and washed well with ether. The filtrates were combined and concentrated under reduced pressure. The residue was dissolved in CH2Cl2, washed with saturated aqueous NaHCO3 and saturated aqueous NaCl in turn, and the organic phase was dried with anhydrous Na2SO4. The solvent was evaporated under reduced pressure to give a light yellow oil, which was solidified by high vacuum treatment. The resulting solid was ground several times with hexane and dried in high vacuum to obtain 1-tert-butyl-2-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate as a white solid (24.5 g, 100% yield). The product characterization data were as follows:(M+1) 245; 1H NMR (CDCl3, 300MHz) δ 4.54-4.37 (m, 2H), 3.75 (s, 3H), 3.70-3.40 (m, 2H), 2.48-2.21 (m, 2H), 2.13-2.0 (m, 1H), 1.46 (s, 3H), 1.41 (s, 6H).

IC 50

Non-cleavable Linker

References

[1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 22, p. 5699 - 5702
[2] Patent: WO2007/113634, 2007, A1. Location in patent: Page/Page column 60-61
[3] Tetrahedron Asymmetry, 2009, vol. 20, # 12, p. 1433 - 1436
[4] Journal of Chemical Research, 2009, # 11, p. 668 - 670
[5] Tetrahedron Letters, 2012, vol. 53, # 30, p. 3847 - 3849

N-Boc-trans-4-Hydroxy-L-proline methyl ester Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from N-Boc-trans-4-Hydroxy-L-proline methyl ester manufacturers

Hebei Chuanghai Biotechnology Co., Ltd
Product
N-Boc-trans-4-Hydroxy-L-proline methyl ester 74844-91-0
Price
US $30.00-10.00/KG
Min. Order
50KG
Purity
99%
Supply Ability
500000kg
Release date
2024-10-24
Hebei Yanxi Chemical Co., Ltd.
Product
N-Boc-trans-4-Hydroxy-L-proline methyl ester 74844-91-0
Price
US $20.00-1.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
20 tons
Release date
2023-11-29
Nanjing Fred Technology Co., Ltd
Product
N-Boc-trans-4-Hydroxy-L-proline methyl ester 74844-91-0
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
1 ton
Release date
2024-01-02

74844-91-0, N-Boc-trans-4-Hydroxy-L-proline methyl esterRelated Search:


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