ChemicalBook CAS DataBase List (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 synthesis

8synthesis methods

Product Name:(S)-2-(3-((2-Isopropylthiazol-4-yl)methyl)-3-methylureido)-3-methylbutanoic acid
CAS Number:154212-61-0
Molecular formula:C14H23N3O3S
Molecular Weight:313.42

N-((N-Methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)carbonyl)-L-valine methyl ester

154248-99-4

154212-61-0

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.

154248-99-4 Synthesis

154248-99-4
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154212-61-0
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Yield:154212-61-0 93%

Reaction Conditions:

Stage #1:N-((N-methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)carbonyl)-L-valine methyl ester with lithium hydroxide in tetrahydrofuran;water at 20; for 1.5 h;
Stage #2: with hydrogenchloride;water in tetrahydrofuran

Steps:

Compound 29
Compound 29; Compound 28 was prepared using a procedure similar to that used to prepare Compound 6 (described in Scheme 4) except that Compound 9 was used instead of Compound 4.To a solution of Compound 28 (0.757 g, 2.31 mmol) in THF (9 mL) at room temperature was added freshly prepared IM LiOH (4.6 mL, 4.6 mmol). After 1.5 h, 1 M HCl (7 mL, 7 mmol) was added and the reaction mixture extracted thoroughly with EtOAc (5 X 15mL). The combined organic layers were dried

References:

GILEAD SCIENCES, INC. WO2008/10921, 2008, A2 Location in patent:Page/Page column 199-200

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