Sodium Hydroxide → 2-Tert-butoxycarbonyloxyamino-thiazole-5-carboxylic acid

HRID 1048909Notes

Reaction equation

HRID 1048909 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][O:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[N:8][C:7]=1C)=[O:5])C.[OH-].[Na+]>O1CCCC1CO>[C:16]([O:15][C:13]([O:12][NH:11][C:9]1[S:10][C:6]([C:4]([OH:5])=[O:3])=[CH:7][N:8]=1)=[O:14])([CH3:19])([CH3:17])[CH3:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21911455Ethyl-2-tert-butoxycarbonyloxyamino-4-methyl-thiazole-5-carboxylate

Product 1

HCID 219112552-Tert-butoxycarbonyloxyamino-thiazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

A stirred solution of ethyl-2-tert-butoxycarbonyloxyamino-4-methyl-thiazole-5-carboxylate (1.1 g, 4.2 mmol) in tetrahydrofuran-methanol (80 mL, 1:1) was treated with a 6N aq. NaOH solution (20 mL, 120 mmol). The mixture was stirred at rt for 24 h. Most of THF and methanol were removed by distillation under reduced pressure and the aq. Solution was acidified with 6 N aq. HCl solution (22 mL). The precipitated solid was filtered, washed with water and ether, air dried followed by drying in vacuo to obtain the title acid (940 mg, 96%) as an off-white solid.

Workup

  1. customMost of THF and methanol were removed by distillation under reduced pressure
  2. filtrationThe precipitated solid was filtered
  3. washwashed with water and ether, air
  4. customdried
  5. customby drying in vacuo
  6. customto obtain the title acid (940 mg, 96%) as an off-white solid

Sources & evidence

ORD record
ord-a195f79b3e8548acb9da2c8db1e0520b
Source dataset
uspto-grants-2016_07
Patent number
US09382219B2

Reaction notes

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