Water → 2-Amino-1,3-thiazole-4-carboxylic acid, N-BOC protected

HRID 2222986Notes

Reaction equation

HRID 2222986 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[S:8][CH:9]=1)=[O:4].O.O.[OH-].[Li+]>O1CCCC1>[C:14]([O:13][C:11]([NH:10][C:7]1[S:8][CH:9]=[C:5]([C:3]([OH:4])=[O:2])[N:6]=1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 7213137Methyl 2-Boc-aminothiazole-4-carboxylate

Product 1

HCID 15020512-Amino-1,3-thiazole-4-carboxylic acid, N-BOC protectedYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-tert-Butoxycarbonylamino-thiazole-4-carboxylic acid methyl ester (15.5 g, 60.01 mmol) was dissolved in 4:1 tetrahydrofuran:water (300 mL) followed by the addition of lithium hydroxide monohydrate (5.29 g, 126.07 mmol). The solution was stirred overnight at room temperature. Tetrahydrofuran was removed under vacuum and the salt was neutralized with 2.0 N aqueous hydrochloric acid. The resulting precipitate was filtered and dried to give 2-tert-butoxycarbonylamino-thiazole-4-carboxylic acid (10.4 g, 71%).

Workup

  1. customTetrahydrofuran was removed under vacuum
  2. filtrationThe resulting precipitate was filtered
  3. customdried

Sources & evidence

ORD record
ord-2e6ade06a8bf4b1e972ddff4a545d660
Source dataset
uspto-grants-2008_05
Patent number
US07371869B2

Reaction notes

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