Benzyl chloroformate → HCID 10554645, compound

HRID 1981938Notes

Reaction equation

HRID 1981938 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([O:16][C:17](=[O:19])[CH3:18])[C:14](=[O:20])[N:13]([CH2:21][CH2:22][N:23](CC3C=CC=CC=3)[CH3:24])[C:12]3[CH:32]=[CH:33][C:34]([CH3:36])=[CH:35][C:11]=3[S:10]2)=[CH:5][CH:4]=1.[CH2:37]([O:44][C:45](Cl)=[O:46])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C1C=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:17](=[O:19])[CH3:18])[C:14](=[O:20])[N:13]([CH2:21][CH2:22][N:23]([C:45]([O:44][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:46])[CH3:24])[C:12]3[CH:32]=[CH:33][C:34]([CH3:36])=[CH:35][C:11]=3[S:10]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 10767858HCID 10767858, compound

Product 1

HCID 10554645HCID 10554645, compoundYield 104.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 10.37 g of (-)-cis-2-(4-methoxyphenyl)-3-acetoxy-5-[2-(N-benzyl-N-methylamino)ethyl]-8-methyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one and 125 ml of benzene is refluxed. A solution of 9 g of benzyloxycarbonyl chloride in 25 ml of benzene is added dropwise to the mixture for 30 minutes, and the mixture is refluxed for 4 hours. Then, the mixture is evaporated under reduced pressure to remove solvent. 11.8 g of (-)-cis-2-(4-methoxyphenyl)-3-acetoxy-5-[2-(N-benzyloxycarbonyl-N-methylamino)ethyl]-8-methyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are obtained as an oil.

Workup

  1. temperatureis refluxed
  2. temperaturethe mixture is refluxed for 4 hours
  3. customThen, the mixture is evaporated under reduced pressure
  4. customto remove solvent

Sources & evidence

ORD record
ord-d84af941d9724716a85c432b790a418e
Source dataset
uspto-grants-1986_06
Patent number
US04594342

Reaction notes

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