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

HRID 32814

Reaction equation

HRID 32814 reaction equation
O.[OH-].[Li+].C([O:6][C:7]([C:9]1[N:10]=[C:11]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[S:12][CH:13]=1)=[O:8])C.Cl>O1CCCC1.O>[C:18]([O:17][C:15]([NH:14][C:11]1[S:12][CH:13]=[C:9]([C:7]([OH:8])=[O:6])[N:10]=1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 22280595Ethyl 2-((tert-butoxycarbonyl)amino)-1,3-thiazole-4-carboxylate

Product 1

HCID 15020512-Amino-1,3-thiazole-4-carboxylic acid, N-BOC protectedYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (20.16 g, 0.48 mol) was added to a stirred solution of 2-tert-butoxycarbonylamino-thiazole-4-carboxylic acid ethyl ester (52.35 g, 0.192 mol) in a mixture of tetrahydrofuran (800 mL) and water (200 mL). The mixture was stirred over night. 1 N Aqueous hydrochloric acid (480 mL) was added and the reaction mixture concentrated in vacuo to remove tetrahydrofuran. The mixture was then diluted with water and filtered. The solid was washed with water, ether and dried overnight to give 2-tert-butoxycarbonylamino-thiazole-4-carboxylic acid (43.9 g, 94%).

Workup

  1. concentrationthe reaction mixture concentrated in vacuo
  2. customto remove tetrahydrofuran
  3. additionThe mixture was then diluted with water
  4. filtrationfiltered
  5. washThe solid was washed with water, ether
  6. customdried overnight

Sources & evidence

ORD record
ord-0b496ff46b594c1e9dc291e3104313e2
Source dataset
uspto-grants-2008_09
Patent number
US07427635B2

Linked notes

Loading…