Hydrochloric Acid → HCID 15093150, compound

HRID 981470Notes

Reaction equation

HRID 981470 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.Cl>C(OCC)(=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 313Hydrochloric AcidHCID 15093148HCID 15093148, compound

Product 1

HCID 15093150HCID 15093150, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.5 g (0.001 mol) of rac-cis-6-(acetyloxy)-6,7-dihydro-7-(4-methoxyphenyl)-4[2-(dimethylamino)ethyl]-3-phenyl-1,4-thiazepin-5(4H)-one and 5 mL of ethyl acetate saturated with hydrogen chloride was stirred at room temperature for 17 hours. The solvent was removed under reduced pressure and the residue was partitioned between water and ammonium hydroxide. The ethyl acetate solution was washed with brine, dried (MgSO4) and removal of the solvent gave 0.3 g (67%) of rac.-cis-6,7-dihydro-6-hydroxy-7-(4-methoxyphenyl)-4-[2(dimethylamino) ethyl]-3-phenyl-1,4-thiazepin-5(4H)-one. Analytical sample was crystallized from ethyl acetate, mp 159°-160°.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between water and ammonium hydroxide
  3. washThe ethyl acetate solution was washed with brine
  4. customdried
  5. custom(MgSO4) and removal of the solvent

Sources & evidence

ORD record
ord-6fb742826b8a4fb0b995f3ab0af3f4b6
Source dataset
uspto-grants-1991_02
Patent number
US04992432

Reaction notes

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