Hydrochloric Acid → 5-Bromo-3-((tert-butoxycarbonyl)amino)thiophene-2-carboxylic acid

HRID 532432Notes

Reaction equation

HRID 532432 reaction equation
[OH-].[Li+].C[O:4][C:5]([C:7]1[S:8][C:9]([Br:20])=[CH:10][C:11]=1[NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:6].Cl>C1COCC1.O>[Br:20][C:9]1[S:8][C:7]([C:5]([OH:6])=[O:4])=[C:11]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57356848Methyl 5-bromo-3-((tert-butoxycarbonyl)amino)thiophene-2-carboxylate

Product 1

HCID 219758545-Bromo-3-((tert-butoxycarbonyl)amino)thiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

An aqueous 2 M lithium hydroxide solution (1 mL) was added to a solution of 5-bromo-3-tert-butoxycarbonylaminothiophene-2-carboxylic acid methyl ester (330.0 mg) in THF/water (1.6 mL/1.6 mL). The solution was stirred at room temperature overnight and was then neutralized with diluted HCl solution, and the solvent was removed in vacuo. The product with the molecular weight of 322.18 (C10H12BrNO4S) was obtained in this way; MS (ESI): 221, 223 (M-Boc+H+).

Workup

  1. customthe solvent was removed in vacuo
  2. customThe product with the molecular weight of 322.18 (C10H12BrNO4S) was obtained in this way

Sources & evidence

ORD record
ord-4c14ad416ab34a00bac65c7b0205a07b
Source dataset
uspto-grants-2014_10
Patent number
US08853208B2

Reaction notes

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