ChemicalBook > CAS DataBase List > Methoxycarbonyl-L-tert-leucine

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

TRC

Product number: M261295
Product name: N-(Methoxycarbonyl)-L-tert-leucine
Packaging: 5g
Price: $955
Updated: 2021/12/16

Usbiological

Product number: 281876
Product name: Methoxycarbonyl-L-tert-leucine
Packaging: 50g
Price: $342
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: AAA0002044
Product name: (S)-2-METHOXYCARBONYLAMINO-3,3-DIMETHYL-BUTYRIC ACID
Purity: 95.00%
Packaging: 25MG
Price: $579
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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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