Phenylacetic Acid → 2-(2-Phenylacetamido)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide

HRID 2227559

Reaction equation

[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11](=[O:13])[NH2:12].[C:14]1([CH2:20][C:21](O)=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.ON1C2C=CC=CC=2N=N1.OC1C2N=NNC=2C=CC=1>ClCCl.CN(C)C=O>[C:11]([C:3]1[C:4]2[CH2:10][CH2:9][CH2:8][CH2:7][C:5]=2[S:6][C:2]=1[NH:1][C:21](=[O:22])[CH2:20][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])[NH2:12]

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of commercially available 2-amino-3-carbamoyl-4,5,6,7-tetrahydrobenzo[b]thiophene (5 mg, 0.026 mmol), phenylacetic acid (7 mg, 0.05 mmol), N-hydroxybenzotriazole (8.5 mg, 0.065 mmol), and N-cyclohexylcarbodiimide-N′-methylpolystyrene (loading about 1.5 mmol/g resin, 50 mg) in dichloromethane (2 ml)/dimethylformamide (0.5 ml) was agitated at 20° C. for 170 h. Afterward tris-(2-aminoethyl)-amine polystyrene (loading about 4 mmol/g resin 40 mg) was added for scavenging the hydroxybenzotriazole and the excess of acid, and the agitation was maintained for additional 24 h.

Workup

temperaturethe excess of acid, and the agitation was maintained for additional 24 h.

Sources & evidence

ORD record: ord-36dc15d5abb34eac8097fefb794fa7d9
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06414013B1

Linked notes

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