Acetic Acid → 2-[[(1,1-Dimethylethoxy)carbonyl]amino]-4,5-dimethyl-3-thiophenecarboxylic acid

HRID 1974989Notes

Reaction equation

HRID 1974989 reaction equation
[C:1]([O:5][C:6]([N:8](C(OC(C)(C)C)=O)[C:9]1[S:10][C:11]([CH3:20])=[C:12]([CH3:19])[C:13]=1[C:14]([O:16]CC)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[OH-].[K+].C(O)(=O)C>O>[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][C:11]([CH3:20])=[C:12]([CH3:19])[C:13]=1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 19100749HCID 19100749, compound

Product 1

HCID 191008122-[[(1,1-Dimethylethoxy)carbonyl]amino]-4,5-dimethyl-3-thiophenecarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 2-bis(t-butoxycarbonyl)amino-4,5-dimethylthiophene3-carboxylate (13.6 g, 34 mmol) was hydrolysed by refluxing in 70 ml of water and 140 ml of methanol with 7.63 g of potassium hydroxide. Addition of 8.1 ml of acetic acid and stirring overnight precipitated 8.27 g (90%) of 2-t-butoxycarbonylamino-4,5-dimethylthiophene-3-carboxylic acid. M.p. 185° C. (dec.). 1H-NMR (DMSO-d6, δ): 1.5 (s, 9H), 2.15 (s, 3H), 2.2 (s, 3H), 10.4 (s, 1H), 13.1 (br.s, 1H).

Workup

  1. customprecipitated 8.27 g (90%) of 2-t-butoxycarbonylamino-4,5-dimethylthiophene-3-carboxylic acid

Sources & evidence

ORD record
ord-e72eababe74d4c8b8864e7609526e540
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

Loading…