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 1461481노트

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HRID 1461481 반응식
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]

참가 물질

4

반응물 2

HCID 7918Acetic AnhydrideHCID 19980840HCID 19980840, 화합물

생성물 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-carboxylate수율 89%

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-a442e888cfe6431899877f0deb59f767
출처 데이터셋
uspto-grants-1991_12
특허 번호
US05075440

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