Triethylamine → HCID 70092375, compound

HRID 654664Notes

Reaction equation

HRID 654664 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([O:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:14](=[O:23])[N:13]([CH2:24][CH2:25][NH:26][CH3:27])[C:12]3[CH:28]=[CH:29][CH:30]=[CH:31][C:11]=3[S:10]2)=[CH:5][CH:4]=1.[CH2:32](N(CC)CC)C.C(Br)[CH:40]=[CH:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[C@@H:15]([O:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:14](=[O:23])[N:13]([CH2:24][CH2:25][N:26]([CH3:32])[CH2:27][CH:40]=[CH:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:12]3[CH:28]=[CH:29][CH:30]=[CH:31][C:11]=3[S:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 98116BromomethylstyreneHCID 70089989HCID 70089989, compound

Product 1

HCID 70092375HCID 70092375, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (+)-cis-2-(4-methoxyphenyl)-3-(ethoxycarbonylmethyl)oxy-5-[2-(methylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (1.0 g), triethylamine (375 mg), cinnamyl bromide (730 mg) and methylene chloride (20 ml) is stirred at room temperature overnight. The reaction mixture is concentrated under reduced pressure, and the resulting residue is purified by silica gel column chromatography (eluent; chloroform: ethanol=20:1) to give (+)-cis-2-(4-methoxyphenyl)-3(ethoxycarbonylmethyl)oxy-5-[2-(N-methyl-N-cinnamylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one as oil product.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customthe resulting residue is purified by silica gel column chromatography (eluent; chloroform: ethanol=20:1)

Sources & evidence

ORD record
ord-5e178d51d15c4dcfaf127d5fa87fa45b
Source dataset
uspto-grants-1992_07
Patent number
US05134139

Reaction notes

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