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
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℃
Safety
- HS Code
- 2933399090
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.
N-Bromosuccinimide Price
- Product number
- PHR3001
- Product name
- Atazanavir Related Compound A
- Purity
- pharmaceutical secondary standard, certified reference material
- Packaging
- 50MG
- Price
- $433
- Updated
- 2025/07/31
- Product number
- 1044356
- Product name
- Atazanavir Related Compound A
- Purity
- United States Pharmacopeia (USP) Reference Standard
- Packaging
- 25mg
- Price
- $1200
- Updated
- 2025/07/31
- Product number
- M261295
- Product name
- N-(Methoxycarbonyl)-L-tert-leucine
- Packaging
- 5g
- Price
- $955
- Updated
- 2021/12/16
- Product number
- 281876
- Product name
- Methoxycarbonyl-L-tert-leucine
- Packaging
- 50g
- Price
- $342
- Updated
- 2021/12/16
- Product number
- AAA0002044
- Product name
- (S)-2-METHOXYCARBONYLAMINO-3,3-DIMETHYL-BUTYRIC ACID
- Purity
- 95.00%
- Packaging
- 25MG
- Price
- $579
- Updated
- 2021/12/16
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
- 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
- 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
- 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