Sodium Hydroxide → N-Boc-amino-4-methylthiazole-5-carboxylic acid

HRID 2279656Notes

Reaction equation

HRID 2279656 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[N:8][C:7]=1[CH3:19])=[O:5])C.[OH-].[Na+]>CO>[C:15]([O:14][C:12]([NH:11][C:9]1[S:10][C:6]([C:4]([OH:5])=[O:3])=[C:7]([CH3:19])[N:8]=1)=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53404548Ethyl 2-[(tert-butoxycarbonyl)amino]-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 2756770N-Boc-amino-4-methylthiazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-tert-butoxycarbonylamino-4-methyl-thiazole-5-carboxylic acid ethyl ester (4.3 g) and sodium hydroxide (10 N, 2.5 mL) in MeOH (80 mL) is heated at 50° C. overnight. The mixture is cooled, concentrated in vacuo, diluted with water and acidified to pH 4-5 with 2 N HCl. The solid is collected by filtration and dried to give the title compound.

Workup

  1. temperatureThe mixture is cooled
  2. concentrationconcentrated in vacuo
  3. additiondiluted with water
  4. filtrationThe solid is collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-723571fde6124a608edfdafd49910edb
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

Loading…