Ethanol → HCID 10074926, compound

HRID 359762Notes

Reaction equation

HRID 359762 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][C:3]=1[S:15][CH:16]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[CH:17]([OH:21])[C:18]([OH:20])=O.C(O[C:34](=[O:36])[CH3:35])(=O)C.[CH2:37](O)[CH3:38].C(OCC)(=O)C.[N:46]1[CH:51]=CC=C[CH:47]=1>>[C:34]([O:21][C@H:17]1[C:18](=[O:20])[N:1]([CH2:38][CH2:37][N:46]([CH3:51])[CH3:47])[C:2]2[CH:7]=[CH:6][C:5]([O:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)=[CH:4][C:3]=2[S:15][C@H:16]1[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)(=[O:36])[CH3:35]

Participants

6

Reactant 5

HCID 702EthanolHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 15687402HCID 15687402, compound

Product 1

HCID 10074926HCID 10074926, compound

Procedure

773 mg of (±)-cis-5-(2-dimethylaminoethyl)-2,3- dihydro-3-hydroxy-2-(4-methoxyphenyl)-8-phenoxy-1 5- benzothiazepin-4(5H)-one (prepared as described in Example 1) were dissolved in 5 ml of pyridine, and 1 ml of acetic anhydride was added at room temperature to the resulting solution. The mixture was then left to stand for 14 hours. At the end of this time, 2 ml of ethanol were added to the reaction mixture, and after the mixture had been left to stand for 30 minutes, 30 ml of ethyl acetate were added. The mixture was then washed with an aqueous solution of sodium bicarbonate and with an aqueous solution of sodium chloride in that order, after which it was dried over anhydrous magnesium sulfate, and concentrated by evaporation under reduced pressure to obtain a concentrate. This concentrate was purified by chromatography through a silica gel column, using a 20 : 1 by volume mixture of methylene chloride and methanol as the eluent, to give the title compound as a solid.

Workup

  1. waitThe mixture was then left
  2. waitafter the mixture had been left
  3. waitto stand for 30 minutes
  4. washThe mixture was then washed with an aqueous solution of sodium bicarbonate and with an aqueous solution of sodium chloride in that order
  5. dry with materialafter which it was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customto obtain a concentrate
  8. customThis concentrate was purified by chromatography through a silica gel column
  9. additionby volume mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-1eec8e16003e4253b80188d277ce41d1
Source dataset
uspto-grants-1991_03
Patent number
US05002942

Reaction notes

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