| Identification | More | [Name]
(S)-2-(3-((2-Isopropylthiazol-4-yl)methyl)-3-methylureido)-3-methylbutanoic acid | [CAS]
154212-61-0 | [Synonyms]
N-[2-Isopropylthiazol-4-ylmethyl(methyl)carbamoyl]-L-valine
(s)-2-(3-((2-isopropylthiazol-4-yl)methyl)-3-methylureido)-3-methylbutanoic acid
(S)-2-(3-((2-ISOPROPYLTHIAZOL-4-YL)METHYL)-3-METHYLUREIDO)-3-METHYLBUTANOIC ACID,98% | [EINECS(EC#)]
680-588-9 | [Molecular Formula]
C14H23N3O3S | [MDL Number]
MFCD07369527 | [Molecular Weight]
313.42 | [MOL File]
154212-61-0.mol |
| Chemical Properties | Back Directory | [Boiling point ]
532.6±40.0 °C(Predicted) | [density ]
1.193 | [storage temp. ]
2-8°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
4.39±0.10(Predicted) | [color ]
Light Yellow to Beige | [InChI]
InChI=1S/C14H23N3O3S/c1-8(2)11(13(18)19)16-14(20)17(5)6-10-7-21-12(15-10)9(3)4/h7-9,11H,6H2,1-5H3,(H,16,20)(H,18,19)/t11-/m0/s1 | [InChIKey]
OSQWRZICKAOBFA-NSHDSACASA-N | [SMILES]
C(O)(=O)[C@H](C(C)C)NC(N(C)CC1=CSC(C(C)C)=N1)=O | [CAS DataBase Reference]
154212-61-0(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
Light Yellow Oil | [Uses]
An intermediate in the synthesis of Ritonavir. | [Uses]
N-[[N-Methyl-N-[(2-isopropyl]-4-thiazolyl)methyl)amino]carbonyl-L-valine Carboxylic Acid (Ritonavir EP Impurity A) is an intermediate in the synthesis of Ritonavir. | [Synthesis]
The general procedure for the synthesis of (S)-2-(3-((2-isopropylthiazol-4-yl)methyl)-3-methylureido)-3-methylbutanoic acid from N-((N-methyl-N-((2-isopropylthiazol-4-yl)methyl)amino)formyl)-L-valine methyl ester was as follows: compound 28 was prepared by reference to the method used for the preparation of compound 6 in Scheme 4, except that compound 9 was substituted for compound 4 as the starting material. Compound 28 (0.757 g, 2.31 mmol) was dissolved in THF (9 mL), and a freshly prepared aqueous 1M LiOH solution (4.6 mL, 4.6 mmol) was slowly added at room temperature. After 1.5 h of reaction, 1M HCl aqueous solution (7 mL, 7 mmol) was added to neutralize the reaction solution. Subsequently, the reaction mixture was extracted several times with EtOAc (5 × 15 mL). All organic layers were combined and dried with anhydrous sodium sulfate. | [References]
[1] Patent: WO2008/10921, 2008, A2. Location in patent: Page/Page column 199-200
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 4, p. 602 - 617
[3] Patent: WO2006/90270, 2006, A1. Location in patent: Page/Page column 10
[4] Patent: US5484801, 1996, A
[5] Patent: US5559158, 1996, A |
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