Potassium Carbonate → HCID 15093150, compound

HRID 981472Notes

Reaction equation

HRID 981472 reaction equation
C([O:4][C@H:5]1[C@@H:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[S:10][CH:9]=[C:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:7]([CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])[C:6]1=[O:31])(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[OH:4][C@H:5]1[C@@H:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[S:10][CH:9]=[C:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:7]([CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])[C:6]1=[O:31]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 15093148HCID 15093148, compound

Product 1

HCID 15093150HCID 15093150, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.3 g (0.003 mol) of (+)-cis-6-(acetyloxy)-6,7-dihydro-7-(4-methoxyphenyl)-4[2-(dimethylamino)ethyl]-3-phenyl-1,4-thiazepin-5(4H)-one and 30 mL 0.5 M potassium carbonate in 45 mL ethanol was stirred at room temperature for one hour. The solvent was removed under reduced pressure and the residue was partitioned between water and ethyl acetate. The ethyl acetate solution was washed with brine and dried (MgSO4). Removal of the solvent gave the crude base, which after recrystallization from ether afforded 1.1 g (94%) of (+)-cis-6,7-dihydro-6-hydroxy-7-(4-methoxyphenyl)-4-[2 -(dimethylamino)ethyl]-3-phenyl-1,4-thiazepin-5(4H)-one, mp 110°-112°, [α]25 +122.72° (C 1.01, MeOH).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between water and ethyl acetate
  3. washThe ethyl acetate solution was washed with brine
  4. dry with materialdried (MgSO4)
  5. customRemoval of the solvent
  6. customgave the crude base, which
  7. customafter recrystallization from ether

Sources & evidence

ORD record
ord-ad25a7e4b48f4b71bd901b8d12f42902
Source dataset
uspto-grants-1991_02
Patent number
US04992432

Reaction notes

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