Potassium Hydroxide → 5-(2-Tert-butoxycarbonylamino-phenylcarbamoyl)-thiophene-2-carboxylic acid
Reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:10](=[O:26])[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:8][CH:9]=1)=[O:4].[OH-].[K+]>CO.O>[C:22]([O:21][C:19]([NH:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[NH:11][C:10]([C:7]1[S:6][C:5]([C:3]([OH:4])=[O:2])=[CH:9][CH:8]=1)=[O:26])=[O:20])([CH3:25])([CH3:23])[CH3:24]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a suspension of 18.5 g (50 mmol) 5-(2-tert-Butoxycarbonylamino-phenyl-carbamoyl)-thiophene-2-carboxylic acid methyl ester in 500 ml MeOH was added within 20 minutes a solution of 5.6 g (100 mmol) potassium hydroxide in 100 ml water. The reaction mixture was stirred at room temperature for 2 d. The MeOH was evaporated and the remaining aqueous solution was extracted three times with ethylacetate and acidified with a 3 N aqueous HCl solution. The precipitation was filtered off, washed with water and dried at 45° C. in high vacuum to yield 14.5 g (40 mmol) 5-(2-tert-butoxycarbonylamino-phenylcarbamoyl)-thiophene-2-carboxylic acid., 1H-NMR (D6-DMSO) δ=1.45 (s, 9H), 7.14 (m, 1H), 7.22 (m, 1H), 7.46 (m, 1H), 7.59 (m, 1H), 7.90 (m, 2H), 8.72 (s, 1H), 9.99 (s, 1H), 13.54 (s, 1H).
Workup
- customThe MeOH was evaporated
- extractionthe remaining aqueous solution was extracted three times with ethylacetate
- customThe precipitation
- filtrationwas filtered off
- washwashed with water
- customdried at 45° C. in high vacuum
Sources & evidence
- ORD record
- ord-fe083d7fc1964a5597f6c4073c73ab34
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07071219B2
Reaction notes
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