Acetic Anhydride → HCID 18606599, compound

HRID 235685Notes

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

Reactant 2

HCID 7918Acetic Anhydride

HCID 18606604HCID 18606604, compound

Product 1

HCID 18606599HCID 18606599, compoundYield 99%

Procedure

A mixture of 3.2 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 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 ethyl acetate (2×50 mL). The combined extracts were washed with brine (50 mL) and dried (magnesium sulfate). Removal of the solvent under reduced pressure gave 3.2 g (99%) 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 -190.81° (C 0.48, methanol).

Workup

customThe excess reagent was removed under reduced pressure and to the residue ice-water
additionwas added
extractionextracted with ethyl acetate (2×50 mL)
washThe combined extracts were washed with brine (50 mL)
dry with materialdried (magnesium sulfate)
customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record: ord-7590c955ee984ab1ae0eeca1be940430
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04640930

Reaction notes

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