O-Xylene → 3-Hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, (2S,3S)-

HRID 487334Notes

Reaction equation

[O:1]1[C@@H:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[C@@H:2]1[C:3]([O:5]C)=O.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[SH:23].C1(C)C(C)=CC=CC=1>CS(O)(=O)=O.CO>[OH:1][C@H:2]1[C:3](=[O:5])[NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23][C@H:7]1[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 10 °C

Procedure

A mixture of 40 g of methyl (2R,3S)-2,3-epoxy-3-(4-methoxyphenyl)propionate, 26.5 g of 2-aminothiophenol and 300 ml of xylene is heated at 110° to 120° C. for 1 hour, whereby the reaction mixture containing methyl (2S,3S)-3-[(2-aminophenyl)thiol]-2-hydroxy-3-(4-methoxylphenyl)propionate is obtained. 380 mg of methanesulfonic acid are added to the mixture and the mixture is refluxed for 7 hours. During the reaction, methanol formed is removed by the azeotropic distillation with xylene. The mixture is cooled to under 10° C. and then stirred for 1 hour. Precipitated crystals are collected by filtration, washed with cooled methanol and then dried, whereby 49.1 g of (2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are obtained. Yield: 84.8% m.p.: 204°-205° C. [α]D20 +115° (c=0.5, dimethylformamide)

Workup

temperatureis heated at 110° to 120° C. for 1 hour
customis obtained
temperaturethe mixture is refluxed for 7 hours
customformed
customis removed by the azeotropic distillation with xylene
customPrecipitated crystals
filtrationare collected by filtration
washwashed with cooled methanol
customdried

Sources & evidence

ORD record: ord-33bca9eaceb44477bc88e1481e2b4642
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05294706

Reaction notes

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