Ethanol → HCID 19100693, compound

HRID 1974986Notes

Reaction equation

HRID 1974986 reaction equation
[C:1]([O:5][C:6]([N:8]([C:16]1[S:17][CH:18]=[C:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]=1[C:21]([O:23]CC)=[O:22])C(OC(C)(C)C)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)C.O.[OH-].[K+]>C(O)(=O)C>[C:1]([O:5][C:6]([NH:8][C:16]1[S:17][CH:18]=[C:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]=1[C:21]([OH:23])=[O:22])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14797Potassium HydroxideHCID 19100690HCID 19100690, compound

Product 1

HCID 19100693HCID 19100693, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl bis(t-butoxycarbonyl)amino-4-phenylthiophene-3-carboxylate (4.37 g, 9.76 mmol), 40 ml of ethanol, 20 ml of water and 2.19 g of potassium hydroxide was heated at reflux for 3 h. The mixture was cooled and acidified with 2.9 ml of--acetic acid. The precipitate was isolated to give 2.70 g (87%) of 2-t-butoxycarbonylamino4-phenylthiophene-3-carboxylic acid. M.p. 183° C. (dec.). 1H-NMR (DMSO-D6, δ): 1.5 (s, 9H), 6.7 (s, 1H), 7.3 (m, 5H), 11.5 (br.s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. temperatureThe mixture was cooled
  4. customThe precipitate was isolated

Sources & evidence

ORD record
ord-5d3793cd22f341d88a265a0cd19f7ba6
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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