| Identification | Back Directory | [Name]
Methoxycarbonyl-L-tert-leucine | [CAS]
162537-11-3 | [Synonyms]
Moc-L-tert-lecine
MOC-L-tert.Leucine
MOC-L-tert. Leucin
N-Moc-L-tert-Leucine
Methylcarbonyl-L-t-Leucine
Atazanavir related coMpound A
Methyl Carbonyl L-tert Leucine
N-Methoxycarbonyl-tert-leucine
Methoxycarbonyl-L-tert-leucine
(S)-N-(METHOXYCARBONYL)-TERT-LEUCINE
N-(Methoxycarbonyl)-3-methyl-L-valine
L-Valine,N-(Methoxycarbonyl)-3-Methyl-
(S)-2-acetamido-3,3-dimethylbutanoic acid
(2S)-2-ACETAMIDO-3,3-DIMETHYLBUTANOIC ACID
(S)-2-(Methoxycarbonyl)-3,3-diMethylbutanoic acid
(S)-2-Methoxycarbonylamino-3,3-dimethylbutyric acid
(S)-2-(MethoxycarbonylaMino)-3,3-diMethylbutanoic acid | [EINECS(EC#)]
1308068-626-2 | [Molecular Formula]
C8H15NO4 | [MDL Number]
MFCD07778455 | [MOL File]
162537-11-3.mol | [Molecular Weight]
189.21 |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [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. | [form ]
powder | [pka]
4.46±0.10(Predicted) | [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℃ |
| Hazard Information | Back Directory | [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]
Notclassified | [Synthesis]
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. |
| Questions And Answer | Back Directory | [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
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