Propionyl chloride → (-)-cis-2-(4-methoxyphenyl)-3-propionyloxy-5-[2-(N-benzyloxycarbonyl-N-methylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

HRID 1381148Notes

Reaction equation

HRID 1381148 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C@H:14]2[C@@H:20]([OH:21])[C:19](=[O:22])[N:18]([CH2:23][CH2:24][N:25]([C:27]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[O:28])[CH3:26])[C:17]3[CH:37]=[CH:38][C:39]([Cl:41])=[CH:40][C:16]=3[S:15]2)=[CH:10][CH:9]=1>N1C=CC=CC=1>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C@H:14]2[C@@H:20]([O:21][C:1](=[O:4])[CH2:2][CH3:3])[C:19](=[O:22])[N:18]([CH2:23][CH2:24][N:25]([C:27]([O:29][CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[O:28])[CH3:26])[C:17]3[CH:37]=[CH:38][C:39]([Cl:41])=[CH:40][C:16]=3[S:15]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 62324Propionyl chlorideHCID 70381263HCID 70381263, compound

Product 1

HCID 70454921(-)-cis-2-(4-methoxyphenyl)-3-propionyloxy-5-[2-(N-benzyloxycarbonyl-N-methylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-oneYield 92.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

490 mg of propionyl chloride are added under ice-cooling to a solution of 2.15 g of (-)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-benzyloxycarbonyl-N-methylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one in 20 ml of pyridine, and the mixture is stirred at room temperature for 3 hours. Then, the mixture is evaporated under reduced pressure. The residue is several times evaporated together with benzene, and ice-water is added to said residue. The aqueous mixture is extracted with ethyl acetate, and the extract is washed with water, 10% hydrochloric acid, water, an aqueous saturated sodium bicarbonate solution and water, successively. Said extract is dried and evaporated under reduced pressure to remove solvent. 2.19 g of (-)-cis-2-(4-methoxyphenyl)-3-propionyloxy-5-[2-(N-benzyloxycarbonyl-N-methylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are obtained as caramel.

Workup

  1. customThen, the mixture is evaporated under reduced pressure
  2. customevaporated together with benzene, and ice-water
  3. additionis added
  4. extractionThe aqueous mixture is extracted with ethyl acetate
  5. washthe extract is washed with water, 10% hydrochloric acid, water
  6. extractionSaid extract
  7. customis dried
  8. customevaporated under reduced pressure
  9. customto remove solvent

Sources & evidence

ORD record
ord-c9936ca03a02425d901642602fbe02ee
Source dataset
uspto-grants-1986_04
Patent number
US04585768

Reaction notes

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