Potassium Hydroxide → HCID 19100820, compound

HRID 1974979Notes

Reaction equation

HRID 1974979 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([CH:19]2[CH2:21][CH2:20]2)[C:13]=1[C:14]([O:16]CC)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N(C(OC(C)(C)C)=O)C1SC=C(C2CC2)C=1C(OCC)=O)=O)(C)(C)C.[OH-].[K+]>CO.O>[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([CH:19]2[CH2:20][CH2:21]2)[C:13]=1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 19100729HCID 19100729, compoundHCID 19100735HCID 19100735, compound

Product 1

HCID 19100820HCID 19100820, compoundYield 170.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred mixture of ethyl 2-t-butoxycarbonylamino-4-cyclopropylthiophene-3-carboxylate (2.7 g, 8.7 mmol) and ethyl 2-bis(t-butoxycarbonyl)amino-4-cyclopropylthiophene-3-carboxylate (4.5 g, 10.9 mmol) in methanol (150 ml), a solution of potassium hydroxide (5.3 g, 95 mmol) in water (55 ml) was added. After heating at 60° C. for 6 h, the mixture was concentrated in vacuo and the residue taken up in water (50 ml) followed by acidification (pH=5) with acetic acid under cooling on ice. The precipitate was filtered off and recrystallized from ethyl acetate/ petroleum ether to afford (4.2 g, 70%) of 2-t-butoxycarbonylamino-4-cyclopropylthiophene-3-carboxylic acid. M.p. 175°-176° C. 1H-NMR (CDCl3, δ): 0.6 (m, 2H), 0.9 (m, 2H), 1.55 (s, 9H), 2.35 (m, 1H), 6.2 (s, 1H), 10.15 (s, 1H).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. temperatureunder cooling on ice
  3. filtrationThe precipitate was filtered off
  4. customrecrystallized from ethyl acetate/ petroleum ether

Sources & evidence

ORD record
ord-6d1f8eb1e6c7455cbfdfb4423ec97720
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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