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

HRID 1247995Notes

Reaction equation

HRID 1247995 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C@H:17]2[C@@H:23]([OH:24])[C:22](=[O:25])[N:21]([CH2:26][CH2:27][N:28]([CH3:31])[CH2:29][CH3:30])[C:20]3[CH:32]=[CH:33][CH:34]=[CH:35][C:19]=3[S:18]2)=[CH:13][CH:12]=1.[Cl:36][C:37]1[CH:45]=[CH:44][C:40]([C:41](Cl)=[O:42])=[CH:39][C:38]=1[N+:46]([O-:48])=[O:47].[C:49]([OH:54])(=[O:53])[C:50]([OH:52])=[O:51]>C(Cl)Cl.CC(C)=O>[C:49]([OH:54])(=[O:53])[C:50]([OH:52])=[O:51].[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([C@H:17]2[C@@H:23]([O:24][C:41](=[O:42])[C:40]3[CH:44]=[CH:45][C:37]([Cl:36])=[C:38]([N+:46]([O-:48])=[O:47])[CH:39]=3)[C:22](=[O:25])[N:21]([CH2:26][CH2:27][N:28]([CH3:31])[CH2:29][CH3:30])[C:20]3[CH:32]=[CH:33][CH:34]=[CH:35][C:19]=3[S:18]2)=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 971Oxalic AcidHCID 8471TriethylamineHCID 1234774-Chloro-3-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 70490285(+)-cis-2-(4-methoxyphenyl)-3-(4-chloro-3-nitrobenzoyloxy)-5-[2-(N-methyl-N-ethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one oxalateYield 62.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

0.5 ml of triethylamine is added to a solution of 430 mg of (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(-N-methyl-N-ethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride in 10 ml of methylene chloride, and 270 mg of 4-chloro-3-nitrobenzoyl chloride are added thereto under ice-cooling and stirring. The mixture is stirred at room temperature overnight. The mixture is washed with water, dried and then condensed under reduced pressure to dryness. The residue is dissolved in acetone, and 90 mg of oxalic acid are added thereto. The mixture is allowed to stand. Crystalline precipitates are collected by filtration and dried. 410 mg of (+)-cis-2-(4-methoxyphenyl)-3-(4-chloro-3-nitrobenzoyloxy)-5-[2-(N-methyl-N-ethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one oxalate are obtained as colorless needles. Yield: 61%.

Workup

  1. additionare added
  2. temperatureunder ice-cooling
  3. stirringThe mixture is stirred at room temperature overnight
  4. washThe mixture is washed with water
  5. customdried
  6. customcondensed under reduced pressure to dryness
  7. customCrystalline precipitates
  8. filtrationare collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-e726d4b89af542f4aef3a323d5ffb954
Source dataset
uspto-grants-1985_06
Patent number
US04521430

Reaction notes

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