Methyl 3-((tert-butoxycarbonyl)amino)thiophene-2-carboxylate → 3-[(tert-Butoxycarbonyl)amino]thiophene-2-carboxylic acid

HRID 1974957Notes

Reaction equation

HRID 1974957 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:13]=[CH:12][S:11][C:10]=1[C:14]([O:16]C)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]>[OH-].[Na+].O1CCCC1>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:13]=[CH:12][S:11][C:10]=1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 18925408Methyl 3-((tert-butoxycarbonyl)amino)thiophene-2-carboxylate

Product 1

HCID 27567723-[(tert-Butoxycarbonyl)amino]thiophene-2-carboxylic acidYield 97.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methyl 3-t-butoxycarbonylaminothiophene-2-carboxylate (15.0 g, 58.3 mmol) was warmed in a mixture of 1 N sodium hydroxide (116.6 ml) and tetrahydrofuran (60 ml) at 50° C. for 16 hours. The mixture was evaporated to a volume of approximately 60 ml, and acidified (pH=2) with hydrochloric acid under cooling in an ice bath. The precipitate was filtered off, washed with water, and dried to afford 13.8 g (97%) of 3-t-butoxycarbonylaminothiophene-2-carboxylic acid. M.p. 168°-169° C. Litt. m.p. 168-169° C. (i. Chem. Res. (S) , 296, 1985). 1H-NMR (DMSO-D6, δ) : 1.49 (s, 9H), 7.76 (d, 1H), 7.85 (d, 1H), 9.45 (s, 1H), 13.45 (s, 1H) .

Workup

  1. customThe mixture was evaporated to a volume of approximately 60 ml
  2. temperatureunder cooling in an ice bath
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-97298e44aec9490b96206d9b35b55e40
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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