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

HRID 1247989Notes

Reaction equation

HRID 1247989 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].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:4](=[O:5])[C:3]3[CH:7]=[CH:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:2]=3[Cl:1])[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 81522Benzoyl chloride, 2-chloro-4-nitro-HCID 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 70381352(+)-cis-2-(4-methoxyphenyl)-3-(2-chloro-4-nitrobenzoyloxy)-5-[2-(N-methyl-N-ethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one oxalateYield 83.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.88 g of 2-chloro-4-nitrobenzoyl chloride in 3 ml of methylene chloride is dropwise added at room temperature 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 stirred for one hour. After the reaction, the mixture is evaporated to remove solvent. The residue is extracted with ethyl acetate, and the extract is washed with water, dried and then evaporated to remove solvent. The oil thus obtained is converted to its oxalate and then recrystallized from ethanol. 1.83 g of (+)-cis-2-(4-methoxyphenyl)-3-(2-chloro-4-nitrobenzoyloxy)-5-[2-(N-methyl-N-ethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one oxalate are thereby obtained as colorless needles. Yield: 83.5%.

Workup

  1. customAfter the reaction
  2. customthe mixture is evaporated
  3. customto remove solvent
  4. extractionThe residue is extracted with ethyl acetate
  5. washthe extract is washed with water
  6. customdried
  7. customevaporated
  8. customto remove solvent
  9. customThe oil thus obtained
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-f9679da0f3904f9c978e7ee43a5aad2b
Source dataset
uspto-grants-1985_06
Patent number
US04521430

Reaction notes

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