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 1461481ノート

反応式

HRID 1461481 の反応式
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]

参加物

4

反応物 2

HCID 7918Acetic AnhydrideHCID 19980840HCID 19980840、化合物

生成物 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-carboxylate収率 89%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-a442e888cfe6431899877f0deb59f767
出典データセット
uspto-grants-1991_12
特許番号
US05075440

反応ノート

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