Acetic Anhydride → 2-Acetoxyethyl 9-(2,3-Dichlorophenyl)-1,1-dioxo-2,3,4,5,6,9-hexahydro-7-methylpyrido [2,3-f][1,4]thiazepine-8-carboxylate

HRID 1461481Notes

Reaction equation

HRID 1461481 reaction equation
C(OC([N:8]1[CH2:14][C:13]2(O)[NH:15][C:16]([CH3:33])=[C:17]([C:27]([O:29][CH2:30][CH2:31][OH:32])=[O:28])[CH:18]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:20]=3[Cl:26])[CH:12]2[S:11](=[O:36])(=[O:35])[CH2:10][CH2:9]1)=O)(C)(C)C.[C:37](OC(=O)C)(=[O:39])[CH3:38]>N1C=CC=CC=1>[Cl:26][C:20]1[C:21]([Cl:25])=[CH:22][CH:23]=[CH:24][C:19]=1[CH:18]1[C:12]2[S:11](=[O:35])(=[O:36])[CH2:10][CH2:9][NH:8][CH2:14][C:13]=2[NH:15][C:16]([CH3:33])=[C:17]1[C:27]([O:29][CH2:30][CH2:31][O:32][C:37](=[O:39])[CH3:38])=[O:28]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 19980840HCID 19980840, compound

Product 1

HCID 150358802-Acetoxyethyl 9-(2,3-Dichlorophenyl)-1,1-dioxo-2,3,4,5,6,9-hexahydro-7-methylpyrido [2,3-f][1,4]thiazepine-8-carboxylateYield 89%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

2-Hydroxyethyl 4-t-butyloxycarbonyl-9-(2,3-dichlorophenyl)-1,1-dioxo-5a-hydroxy-2,3,4,5,5a,6,9,9a-octahydro-7-methylpyrido[2,3-f][1,4]thiazepine-8-carboxylate (0.500 g, 0.97 mmole) from Example 18, was dissolved in 5 mL of pyridine and 5mL of acetic anhydride, and stirred for 2 hours. The solvents were removed under reduced pressure, and the residue was slurried in 25 mL of ethyl acetate and cooled to 0° C., after which the mixture was saturated with gaseous HCl. After 90 minutes, the reaction was poured into 30 mL of 4N NaOH. The ethyl acetate layer was separated and dried with brine, and the aqueous layer was extracted with 2×30 mL of chloroform. The combined organic extracts were dried with sodium sulfate and evaporated, and the residue was chromatographed (2% methanol, 0.1% ammonia in chloroform, silica gel) to give the product as a white solid (0.351 g, 89% yield).

Workup

  1. customThe solvents were removed under reduced pressure
  2. additionthe reaction was poured into 30 mL of 4N NaOH
  3. customThe ethyl acetate layer was separated
  4. dry with materialdried with brine
  5. extractionthe aqueous layer was extracted with 2×30 mL of chloroform
  6. dry with materialThe combined organic extracts were dried with sodium sulfate
  7. customevaporated
  8. customthe residue was chromatographed (2% methanol, 0.1% ammonia in chloroform, silica gel)

Sources & evidence

ORD record
ord-a442e888cfe6431899877f0deb59f767
Source dataset
uspto-grants-1991_12
Patent number
US05075440

Reaction notes

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