Triethylamine → (+)-cis-2-(4-methoxyphenyl)-3-(4-chloro-2-nitrobenzoyloxy)-5-[2-(N-methyl-N-ethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one oxalate

HRID 1247990Notes

Reaction equation

HRID 1247990 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.Cl.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C@H:23]2[C@@H:29]([OH:30])[C:28](=[O:31])[N:27]([CH2:32][CH2:33][N:34]([CH3:37])[CH2:35][CH3:36])[C:26]3[CH:38]=[CH:39][CH:40]=[CH:41][C:25]=3[S:24]2)=[CH:19][CH:18]=1.C(N(CC)CC)C.[C:49]([O-:54])(=[O:53])[C:50]([O-:52])=[O:51]>C(Cl)Cl>[C:49]([OH:54])(=[O:53])[C:50]([OH:52])=[O:51].[CH3:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([C@H:23]2[C@@H:29]([O:30][C:6](=[O:7])[C:5]3[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][C:4]=3[N+:11]([O-:13])=[O:12])[C:28](=[O:31])[N:27]([CH2:32][CH2:33][N:34]([CH3:37])[CH2:35][CH3:36])[C:26]3[CH:38]=[CH:39][CH:40]=[CH:41][C:25]=3[S:24]2)=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 71081OxalateHCID 108677844-Chloro-2-nitrobenzoyl chlorideHCID 70381102(+)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-methyl-N-ethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride

Product 1

HCID 70490131(+)-cis-2-(4-methoxyphenyl)-3-(4-chloro-2-nitrobenzoyloxy)-5-[2-(N-methyl-N-ethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one oxalateYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.88 g of 4-chloro-2-nitrobenzoyl chloride in 3 ml of methylene chloride is added to a mixture of 1.41 g of (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-methyl-N-ethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride, 15 ml of methylene chloride and 1 ml of triethylamine. The mixture is treated in the same manner as described in Example 28-(2). The crude product is converted to its oxalate and then recrystallized from methanol. 1.9 g of (+)-cis-2-(4-methoxyphenyl)-3-(4-chloro-2-nitrobenzoyloxy)-5-[2-(N-methyl-N-ethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one oxalate are thereby obtained as colorless prisms. Yield: 86.4%.

Workup

  1. additionThe mixture is treated in the same manner
  2. customrecrystallized from methanol

Sources & evidence

ORD record
ord-f227c5f31b034c3f8cd2554d8db8a9ad
Source dataset
uspto-grants-1985_06
Patent number
US04521430

Reaction notes

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