Acetic Anhydride → 5-[2-(Dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydronaphtho[1,2-b][1,4]thiazepin-3-yl acetate
Reaction equation
Cl.[OH:2][C@@H:3]1[C@H:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[S:8][C:7]2[C:18]3[C:23]([CH:24]=[CH:25][C:6]=2[N:5]([CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])[C:4]1=[O:31])=[CH:22][CH:21]=[CH:20][CH:19]=3.[C:32](OC(=O)C)(=[O:34])[CH3:33]>>[C:32]([O:2][C@@H:3]1[C@H:9]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[S:8][C:7]2[C:18]3[C:23]([CH:24]=[CH:25][C:6]=2[N:5]([CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])[C:4]1=[O:31])=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:34])[CH3:33]Participants
Procedure
A mixture of 3.6 g of (+)-cis-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-5-[2-(dimethylamino)ethyl]naphtho[1,2-b]-1,4-thiazepin-4(5H)-one hydrochloride and 6 mL acetic anhydride was stirred at 100° for 7 hours. The excess reagent was removed under reduced pressure and to the residue ice-water was added. The resulting suspension was made basic with concentrated ammonium hydroxide and extracted with methylene chloride. The combined methylene chloride solutions were washed with water (15 mL) and dried (magnesium sulfate). Removal of the solvent at reduced pressure gave 3.6 g (98%) of (+)-cis-3-(acetyloxy)-2,3-dihydro-2-(4-methoxyphenyl)-5-[2-(dimethylamino)ethyl]naphtho[1,2-b]-1,4-thiazepin-4(5H)-one as an amorphous compound, [α]D25 +11.02° (C 0.56, MeOH).
Workup
- customThe excess reagent was removed under reduced pressure and to the residue ice-water
- additionwas added
- extractionextracted with methylene chloride
- washThe combined methylene chloride solutions were washed with water (15 mL)
- dry with materialdried (magnesium sulfate)
- customRemoval of the solvent at reduced pressure
Sources & evidence
- ORD record
- ord-a7f14d812a9745108a41119d1697d7db
- Source dataset
- uspto-grants-1987_03
- Patent number
- US04652561
Reaction notes
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