(S)-2-(3-((2-Isopropylthiazol-4-yl)methyl)-3-methylureido)-3-methylbutanoic acid Chemical Properties

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)

(S)-2-(3-((2-Isopropylthiazol-4-yl)methyl)-3-methylureido)-3-methylbutanoic acid Usage And Synthesis

Chemical Properties

Light Yellow Oil

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

(S)-2-(3-((2-Isopropylthiazol-4-yl)methyl)-3-methylureido)-3-methylbutanoic acid(154212-61-0)Related Product Information

• Pirimiphos-methyl
• Valine
• Methylchloroisothiazolinone/methylisothiazolinone mixture (MCIT/MIT)
• Methyl salicylate
• L-Valine
• 2-Aminothiazole-4-acetic acid
• DL-Norvaline
• Benzothiazole
• Kresoxim-methyl
• 1,1'-Carbonyldiimidazole
• Methyl acetate
• METSULFURON METHYL
• Tribenuron methyl
• ((5-Thiazolyl)methyl)-(4-nitrophenyl)carbonate
• [(1S,3S,4S)-4-Amino-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-carbamic acid 1,1-dimethylethyl ester
• Thiophanate-methyl
• Methyl
• Ritonavir EP Impurity O