Acetic Anhydride → HCID 18606599, compound

HRID 235684Notes

Reaction equation

HRID 235684 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

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 18606604HCID 18606604, compound

Product 1

HCID 18606599HCID 18606599, compoundYield 99%

Procedure

A mixture of 0.4 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 8 mL of acetic anhydride was heated at 100° for 17 hours. The reaction mixture was concentrated to dryness and to the residue water, followed by concentrated ammonium hydroxide were added. The aqueous suspension was extracted with ethyl acetate. The ethyl acetate solution was washed with brine, dried (magnesium sulfate) and removal of the solvent gave 0.4 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. A sample of this compound was crystallized from ether, mp. 111°-112°.

Workup

  1. temperaturewas heated at 100° for 17 hours
  2. concentrationThe reaction mixture was concentrated to dryness and to the residue water
  3. additionwere added
  4. extractionThe aqueous suspension was extracted with ethyl acetate
  5. washThe ethyl acetate solution was washed with brine
  6. customdried
  7. custom(magnesium sulfate) and removal of the solvent

Sources & evidence

ORD record
ord-493f807f24364b9cbea57cb096634575
Source dataset
uspto-grants-1987_02
Patent number
US04640930

Reaction notes

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