Benzoyl chloride, 2-chloro-4-nitro- → (-)-cis-2-(4-methoxyphenyl)-3-(2-chloro-4-nitrobenzoyloxy)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

HRID 1247996Notes

Reaction equation

HRID 1247996 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([OH:16])[C:14](=[O:17])[NH:13][C:12]3[CH:18]=[CH:19][CH:20]=[CH:21][C:11]=3[S:10]2)=[CH:5][CH:4]=1.[Cl:22][C:23]1[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[C@@H:15]([O:16][C:25](=[O:26])[C:24]3[CH:28]=[CH:29][C:30]([N+:32]([O-:34])=[O:33])=[CH:31][C:23]=3[Cl:22])[C:14](=[O:17])[NH:13][C:12]3[CH:18]=[CH:19][CH:20]=[CH:21][C:11]=3[S:10]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 81522Benzoyl chloride, 2-chloro-4-nitro-HCID 27336733-Hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, (2S,3S)-

Product 1

HCID 70381329(-)-cis-2-(4-methoxyphenyl)-3-(2-chloro-4-nitrobenzoyloxy)-2,3-dihydro-1,5-benzothiazepin-4(5H)-oneYield 99.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3.01 g of (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are dissolved in 50 ml of pyridine, and 2.31 g of 2-chloro-4-nitrobenzoyl chloride are added thereto under ice-cooling and stirring. The mixture is stirred at room temperature overnight. The mixture is poured into ice-water and then extracted with ethyl acetate. The extract is washed with 10% hydrochloric acid and water, dried and then evaporated under reduced pressure to remove solvent. The residue is purified by silica gel chromatography (solvent, chloroform:methanol=100:1). 4.81 g of (-)-cis-2-(4-methoxyphenyl)-3-(2-chloro-4-nitrobenzoyloxy)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are obtained as a pale yellow powder. Yield: 99%.

Workup

  1. temperatureunder ice-cooling
  2. stirringThe mixture is stirred at room temperature overnight
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with 10% hydrochloric acid and water
  5. customdried
  6. customevaporated under reduced pressure
  7. customto remove solvent
  8. customThe residue is purified by silica gel chromatography (solvent, chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-7cefb0a1a25d43c8b0966a7754562ab1
Source dataset
uspto-grants-1985_06
Patent number
US04521430

Reaction notes

Loading…