Sodium Hydroxide → 2-N-Boc-Amino-Thiazole-5-Carboxylic Acid

HRID 1874006Notes

Reaction equation

HRID 1874006 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][C:11]([C:14]([O:16]CC)=[O:15])=[CH:12][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][C:11]([C:14]([OH:16])=[O:15])=[CH:12][N:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 7213140Ethyl 2-((tert-butoxy(hydroxy)methylidene)amino)-1,3-thiazole-5-carboxylate

Product 1

HCID 222714422-N-Boc-Amino-Thiazole-5-Carboxylic AcidYield 101%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a vigorously stirred suspension of ethyl 2-(tert-butoxycarbonylamino)thiazole-5-carboxylate (4.2 g, 15 mmol) in methanol (11 mL) was added 2 M aqueous solution of NaOH (22 mL, 44.0 mmol). The suspension was stirred at room temperature overnight. The mixture was concentrated in vacuo to remove methanol. The residual aqueous suspension was acidified with 6 N aqueous solution of HCl to pH ˜1-2. The mixture was stirred and occasionally sonicated for 1 hr. The solid was filtered, washed with water, and dried to give 2-(tert-butoxycarbonylamino)thiazole-5-carboxylic acid (3.7 g, 100% yield) as a white solid. MS found: (M+H-Boc)+=145.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto remove methanol
  3. stirringThe mixture was stirred
  4. customoccasionally sonicated for 1 hr
  5. filtrationThe solid was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-09a7564e41b348dd8398446661c3ba65
Source dataset
uspto-grants-2012_11
Patent number
US08304539B2

Reaction notes

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