Diisopropylethylamine → 2-[(7-Hydroxy-benzo[b]thiophene-6-carbonyl)-amino]-2-methyl-propionic acid methyl ester
Reaction equation
[OH:1][C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]=[CH:4][C:3]=1[C:11]([OH:13])=O.Cl.[CH3:15][O:16][C:17](=[O:22])[C:18]([NH2:21])([CH3:20])[CH3:19].C(N(C(C)C)C(C)C)C.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[CH3:15][O:16][C:17](=[O:22])[C:18]([NH:21][C:11]([C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[CH:9][S:8][C:7]=2[C:2]=1[OH:1])=[O:13])([CH3:20])[CH3:19]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1.40 g 7-hydroxy-benzo[b]thiophene-6-carboxylic acid in 20 ml N,N-dimethylformamide were added 0.21 g 1-hydroxy-benzotriaziole and 1.42 g 2-amino-2-methyl-propionic acid methyl ester hydrochloride. At 0° C. 6.4 ml (4.99 g) ethyl-diiso-propyl-amine and 2.22 g (3-dimethylamino-propyl)-ethyl-carbodiimide hydrochloride were added. After 2 days at room temperature the reaction mixture was concentrated in vacuo, and the resulting residue was diluted with ethyl acetate and washed with brine. The organic layer was dried over magnesium sulphate and concentrated. The resulting residue was purified by flash chromatography (silica, heptane/ethyl acetate) to afford 0.84 g 2-[(7-hydroxy-benzo[b]thiophene-6-carbonyl)-amino]-2-methyl-propionic acid methyl ester.
Workup
- customAt 0° C
- concentrationAfter 2 days at room temperature the reaction mixture was concentrated in vacuo
- additionthe resulting residue was diluted with ethyl acetate
- washwashed with brine
- dry with materialThe organic layer was dried over magnesium sulphate
- concentrationconcentrated
- customThe resulting residue was purified by flash chromatography (silica, heptane/ethyl acetate)
Sources & evidence
- ORD record
- ord-4fd7b0099a0542fd8d2b8b643120babf
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08980938B2
Reaction notes
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