Acetic Acid → HCID 19100810, compound

HRID 1974976Notes

Reaction equation

HRID 1974976 reaction equation
[C:1]([O:5][C:6]([N:8](C(OC(C)(C)C)=O)[C:9]1[S:10][CH:11]=[C:12]([CH:19]([CH3:21])[CH3:20])[C:13]=1[C:14]([O:16]CC)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].C(O)(=O)C>CO.O>[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([CH:19]([CH3:21])[CH3:20])[C:13]=1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 19100779HCID 19100779, compound

Product 1

HCID 19100810HCID 19100810, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A solution of ethyl 2-bis(t-butoxycarbonyl)amino-4-isopropylthiophene-3-carboxylate (22.5 g, 55 mmol) in methanol (425 ml) was stirred and a solution of potassium hydroxide (14.5 g, 259 ml) in water (145 ml) was added. The mixture was heated at 80° C. for 16 h, cooled to 0° C. and acidified (pH=5) with glacial acetic acid. The precipitate was filtered off and recrystallized from ethyl acetate/petroleum ether to afford 12.4 g (80%) of 2-t-butoxycarbonylamino-4-isopropylthiophene-3-carboxylic acid. M.p. 205°-206° C. 1H-NMR (CDCl3, δ): 1.25 (d, 6H) 1.55 (s, 9H), 3.6 (m, 1H) 6.45 (s, 1H), 7.25 (s, 1H), 10.2 (s, 1H).

Workup

  1. temperaturecooled to 0° C.
  2. filtrationThe precipitate was filtered off
  3. customrecrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-65eedf8161d04756a51b5c7e4ebf06c4
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

Loading…