Methyl (2R,3S)-3-(4-methoxyphenyl)-2-oxiranecarboxylate → HCID 15593400, compound

HRID 36307Notes

Reaction equation

HRID 36307 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[SH:9].[O:10]1[C@@H:16]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[C@@H:11]1[C:12](OC)=[O:13]>>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:12](=[O:13])[C@H:11]([OH:10])[C@H:16]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[S:9][C:3]=2[CH:4]=1

Participants

3

Reactant 2

HCID 158607Methyl (2R,3S)-3-(4-methoxyphenyl)-2-oxiranecarboxylateHCID 27375182-Amino-5-chlorobenzenethiol

Product 1

HCID 15593400HCID 15593400, compound

Procedure

In the same way as in Example 1, the reaction between 2-amino-5-chlorothiophenol and methyl (-)-(2R,3S)-2,3-epoxy-3-(4-methoxyphenyl)propionate affords (+)-(2S,3S)-8-chloro-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-5H-1,5-benzothiazepine-4-one. Melting point: 237°-241° C. [α]D20 =+91.9° (c=0.1; DMF).

Sources & evidence

ORD record
ord-e2cf6e44e19d4268b10b092f8a2af638
Source dataset
uspto-grants-1995_05
Patent number
USRE034935

Reaction notes

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