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

HRID 2201968Notes

Reaction equation

HRID 2201968 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+]>O1CCCC1CO>[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 Acid

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

The second step involves treating a stirred solution of ethyl 2-[(tert-butoxycarbonyl)amino]-1,3-thiazole-5-carboxylate in tetrahydrofuran-methanol with 6N aqueous sodium hydroxide solution at room temperature for 24 hours. Most of the tetrahydrofuran-methanol were removed by distillation under reduced pressure and the aqueous solution was acidified with 6N hydrochloric acid to obtain a solid which was filtered, washed with water and ether, then air dried, followed by drying in vacuo to obtain 2-[(tert-butoxycarbonyl)amino]-1,3-thiazole-5-carboxylic acid.

Workup

  1. customMost of the tetrahydrofuran-methanol were removed by distillation under reduced pressure
  2. customto obtain a solid which
  3. filtrationwas filtered
  4. washwashed with water and ether
  5. customair dried
  6. customby drying in vacuo

Sources & evidence

ORD record
ord-1239c6fb975d4b24b562a0bf7be81750
Source dataset
uspto-grants-2016_06
Patent number
US09365526B2

Reaction notes

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