Oxalate → HCID 70044869, compound

HRID 2259404Notes

Reaction equation

HRID 2259404 reaction equation
[C:1]([O:4][CH:5]([CH:9]([S:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[NH:26][CH2:27][CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][N:33](C2C=CC=CC=2)[CH2:32][CH2:31]1)[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)[C:6](O)=[O:7])(=[O:3])[CH3:2].[C:42]([O-:47])(=[O:46])[C:43]([O-:45])=[O:44]>>[C:42]([O-:47])(=[O:46])[C:43]([O-:45])=[O:44].[C:1]([O:4][C@H:5]1[C:6](=[O:7])[N:26]([CH2:27][CH2:28][CH2:29][N:30]2[CH2:31][CH2:32][NH:33][CH:34]([C:43]3[CH:42]=[CH:10][CH:9]=[CH:5][CH:6]=3)[CH2:35]2)[C:20]2[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:19]=2[S:18][C@H:9]1[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 71081OxalateHCID 54362570HCID 54362570, compound

Product 2

HCID 71081OxalateHCID 70044869HCID 70044869, compoundYield 48.4%

Procedure

2-Acetoxy-3-[5-chloro -2-[3-(4-phenylpiperazin-1-yl) propyl]aminophenylthio]-3-(4-methoxyphenyl)propionic acid (VT b+VE b, threo/erythro=8.61/1) (2.006 g, 3.353 mmol) is subjected to a ring closure reaction in a similar manner to that described in Example 13 to obtain crude product (cis-VIb +trans-VIb) (1.941 g). This crude product is converted to its oxalate, which is recrystallized to obtain oxalate of (+)-cis-3-acetoxy-8-chloro-2,3-dihydro-2-(4-methoxyphenyl)-5-[3-phenylpiperazin-1-yl]propyl -1,5-benzothiazepine- 4(5H)-one (cis-VIb) (1. 298 g, yield=48.4%) as colorless prism-shaped crystals.

Workup

  1. customto obtain crude product (cis-VIb +trans-VIb) (1.941 g)
  2. customis recrystallized

Sources & evidence

ORD record
ord-5ccf2e00d6f2462bb59fb7a698d9638c
Source dataset
uspto-grants-1995_12
Patent number
US05473066

Reaction notes

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