HCID 19100716, compound → HCID 19100731, compound

HRID 1974997Notes

Reaction equation

HRID 1974997 reaction equation
[C:1]([O:5][C:6]([N:8]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:9]1[C:13]([C:14]#[N:15])=[CH:12][S:11][C:10]=1[C:16]([O:18]C)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[K+]>[C:23]([O:22][C:20]([N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:9]1[C:13]([C:14]#[N:15])=[CH:12][S:11][C:10]=1[C:16]([OH:18])=[O:17])=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 1

HCID 19100716HCID 19100716, compound

Product 1

HCID 19100731HCID 19100731, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 3-bis(t-butoxycarbonyl)amino-4-cyanothiophene-2-carboxylate (38 g, 99.5 mmol) in methanol (160 ml) and 2N potassium hydroxide (50 ml) was heated at 50° C. for 3 h. The methanol was evaporated and the mixture was acidified (pH=5) with acetic acid. The mixture was extracted with ether, dried and concentrated in vacuo. The residue was triturated with petroleum ether and the crystallinic fraction was filtered off to give 32 g (87%) of 3-bis(t-butoxycarbonyl)amino-4-cyanothiophene-2-carboxylic acid. M.p. 159°-160° C. 1H-NMR (CDCl3, δ): 1.45 (s, 18H), 8.1 (s, 1H), 8.5 (br.s, 1H).

Workup

  1. customThe methanol was evaporated
  2. extractionThe mixture was extracted with ether
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with petroleum ether
  6. filtrationthe crystallinic fraction was filtered off

Sources & evidence

ORD record
ord-954177a2d59647808774e99886c7e307
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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