(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

154248-99-4 Synthesis

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

154248-99-4
34 suppliers
$85.00/2mg

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

154212-61-0
221 suppliers
$5.00/1g

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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