Water → HCID 13251127, 화합물

HRID 1912733노트

반응식

HRID 1912733 반응식
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C:11]2=[O:21])[CH2:3]1.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.CCOC(C)=O.O>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28]([O:1][C@H:2]2[CH2:19][CH2:18][C@@:17]3([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]4[C@@H:16]3[CH2:15][CH2:14][C@@:12]3([CH3:13])[C@H:8]4[CH2:9][CH2:10][C:11]3=[O:21])[CH2:3]2)(=[O:30])=[O:29])=[CH:24][CH:23]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 5881DehydroepiandrosteroneHCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl Acetate

생성물 1

HCID 13251127HCID 13251127, 화합물수율 96%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

실험 절차

To a solution of 3β-hydroxyandrost-5-en-17-one (10.00 g) in pyridine (66 mL), toluene-4-sulfonyl chloride (13.20 g) and DMAP (10 mg) were added at 0° C. under stirring. The reaction was allowed to warm to room temperature and stirred for 15 hr. After dilution with EtOAc (300 mL) the mixture was poured into iced water. The organic layer was separated, washed with 1N H2SO4, water and brine, dried and evaporated to dryness to give 3β-(p-toluensulfonyloxy)androst-5-en-17-one (14.70 g, 96%), as a white solid. 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 7.81 (2H, m), 7.48 (2H, m), 5.35 (1H, m), 4.26 (1H, m), 2.46 (3H, s), 2.54-0.93 (19H, m), 1.05 (3H, s), 0.85 (3H, s).

후처리

  1. stirringstirred for 15 hr
  2. customThe organic layer was separated
  3. washwashed with 1N H2SO4, water and brine
  4. customdried
  5. customevaporated to dryness

출처 및 근거

ORD 기록
ord-cfe8272fc9fa45ea98b649f2831b98cb
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609644B2

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