Acetic Anhydride → HCID 18606599, compound
Reaction equation
Cl.[CH3:2][N:3]([CH3:31])[CH2:4][CH2:5][N:6]1[C:13](=[O:14])[C@H:12]([OH:15])[C@H:11]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[S:10][C:9]2=[CH:24][CH:25]=[CH:26][C:27]3=[CH:28][CH:29]=[CH:30][C:7]1=[C:8]23.[C:32](OC(=O)C)(=[O:34])[CH3:33]>>[C:32]([O:15][C@@H:12]1[C@H:11]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[S:10][C:9]2=[CH:24][CH:25]=[CH:26][C:27]3=[CH:28][CH:29]=[CH:30][C:7](=[C:8]23)[N:6]([CH2:5][CH2:4][N:3]([CH3:2])[CH3:31])[C:13]1=[O:14])(=[O:34])[CH3:33]Participants
Procedure
A mixture of 3.4 g of (+)-cis-2,3-dihydro-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)naphtho[1,8-bc]-1,5-thiazocin-4(5H)-one hydrochloride and 60 mL of acetic anhydride was stirred under nitrogen at 100° for 17 hours. The excess of reagent was removed under reduced pressure, then to the residue ice-water was added and made basic with 10% sodium hydroxide. The resulting suspension was extracted with ether (3×75 mL) and the combined ether solutions were washed with brine and dried (magnesium sulfate). Removal of the solvent under reduced pressure gave 3.1 g (90%) of (+)-cis-3-(acetyloxy)-2,3-dihydro-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)naphtho[1,8-bc]-1,5-thiazocin-4(5H)-one as an amorphous compound, [α]D25 +187.94° (C 0.47, methanol).
Workup
- customThe excess of reagent was removed under reduced pressure
- additionto the residue ice-water was added
- extractionThe resulting suspension was extracted with ether (3×75 mL)
- washthe combined ether solutions were washed with brine
- dry with materialdried (magnesium sulfate)
- customRemoval of the solvent under reduced pressure
Sources & evidence
- ORD record
- ord-44ed807f3b174132bf646c38f4d1e866
- Source dataset
- uspto-grants-1987_02
- Patent number
- US04640930
Reaction notes
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