Estradiol → beta-Estradiol diacetate

HRID 1357473

반응식

HRID 1357473 반응식
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][C@@:9]12[C@@H:25]([OH:26])[CH2:24][CH2:23][C@H:22]1[C@H:21]1[C@@H:12]([C:13]3[CH:14]=[CH:15][C:16]([OH:27])=[CH:17][C:18]=3[CH2:19][CH2:20]1)[CH2:11][CH2:10]2.[CH3:28][C:29](C)=[O:30].C(Cl)Cl>N1C=CC=CC=1>[CH3:2][C:1]([O:26][CH:25]1[C:9]2([CH3:8])[CH2:10][CH2:11][CH:12]3[C:13]4[CH:14]=[CH:15][C:16]([O:27][C:29]([CH3:28])=[O:30])=[CH:17][C:18]=4[CH2:19][CH2:20][CH:21]3[CH:22]2[CH2:23][CH2:24]1)=[O:3]

참가 물질

5

반응물 3

HCID 5757EstradiolHCID 7918Acetic AnhydrideHCID 21584124Propan-2-one--dichloromethane (1/1)

생성물 1

HCID 3264beta-Estradiol diacetate수율 95%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

Under nitrogen, acetic anhydride (50 mL, 264.5 mmol) was added to a solution of estradiol (1a) (20.0 g, 73.43 mmol) in dry pyridine (200 mL). The reaction mixture was stirred at room temperature overnight (16 h). The next morning, analysis by tlc (5% acetone/CH2Cl2) indicated a complete reaction. The mixture was cooled in an ice bath and the excess acetic anhydride quenched by addition of methanol (25 mL). The mixture was stirred at 0° C. for one hour and then allowed to warm to room temperature. The solvents were removed in vacuo and the solid residue crystallized from hot methanol to give the pure diacetate (2a) (24.87 g, 95%).

후처리

  1. customa complete reaction
  2. temperatureThe mixture was cooled in an ice bath
  3. customthe excess acetic anhydride quenched by addition of methanol (25 mL)
  4. stirringThe mixture was stirred at 0° C. for one hour
  5. temperatureto warm to room temperature
  6. customThe solvents were removed in vacuo
  7. customthe solid residue crystallized from hot methanol

출처 및 근거

ORD 기록
ord-52a277e776e947bc82b54159aa408f4e
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06593321B2

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