Acetic Anhydride → HCID 10554645, compound

HRID 1981936Notes

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])[N:13]([CH2:18][CH2:19][N:20]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[CH3:21])[C:12]3[CH:32]=[CH:33][C:34]([CH3:36])=[CH:35][C:11]=3[S:10]2)=[CH:5][CH:4]=1.[C:37](OC(=O)C)(=[O:39])[CH3:38]>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:37](=[O:39])[CH3:38])[C:14](=[O:17])[N:13]([CH2:18][CH2:19][N:20]([C:22]([O:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[O:23])[CH3:21])[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

Conditions

Temperature: 100 °C

Procedure

A mixture of 2.49 g of (±)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-benzyloxycarbonyl-N-methylamino)ethyl]-8-methyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, 15 ml of acetic anhydride and 5 ml of pyridine is stirred at 100° C. for 2 hours. The mixture is evaporated under reduced pressure to remove acetic anhydride and pyridine. Toluene is added to the residue, and the mixture is evaporated under reduced pressure to remove solvent (This operation is repeated again). 3.08 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

customThe mixture is evaporated under reduced pressure
customto remove acetic anhydride and pyridine
additionToluene is added to the residue
customthe mixture is evaporated under reduced pressure
customto remove solvent (This operation

Sources & evidence

ORD record: ord-7e2ec0a503c14f9cad8c5531c64e14f2
Source dataset: uspto-grants-1986_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04594342

Reaction notes

Loading…