[Cl:1][CH2:2][C:3]([NH:5][CH:6](O)[C:7]([OH:9])=[O:8])=[O:4].S(=O)(=O)(O)O.C(O)(=O)C.[S:20]1[CH2:24][CH2:23][C:22]2[CH:25]=[CH:26][CH:27]=[CH:28][C:21]1=2>O>[Cl:1][CH2:2][C:3]([NH:5][CH:6]([C:26]1[CH:27]=[CH:28][C:21]2[S:20][CH2:24][CH2:23][C:22]=2[CH:25]=1)[C:7]([OH:9])=[O:8])=[O:4]N-Chloroacetyl-α-hydroxyglycine (6.5 g., 0.038 mole) was added to a cold, stirred mixture of concentrated sulphuric acid (1.5 ml.) and glacial acetic acid (15 ml.) followed, after five minutes, by the dropwise addition of 2,3-dihydrobenzo(b)thiophen (98%, 4.1 g., 0.03 mole). The reaction mixture was stirred at ambient temperature for five hours, then water (75 ml.) was added to the resulting suspension and the mixture thoroughly stirred. Filtration gave a solid which was washed successively with water, diethyl ether and hexane, then dried, to afford DL-α-chloroacetamido-2,3-dihydro-5-benzo(b)thienylacetic acid (5.6 g.), m.p. 173°-175° C.
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