Hydrochloric Acid → HCID 86733309, 화합물

HRID 1606377노트

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HRID 1606377 반응식
[OH:1][C@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@H:8]3[CH2:9][CH:10]=[C:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.Cl>N1C=CC=CC=1>[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30]([O:1][C@H:2]2[CH2:21][CH2:20][C@@:19]3([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]4[C@@H:18]3[CH2:17][CH2:16][C@@:15]3([CH3:23])[C@H:8]4[CH2:9][CH:10]=[C:11]3[C:12](=[O:14])[CH3:13])[CH2:3]2)(=[O:32])=[O:31])=[CH:26][CH:25]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 1775252(3β,5α)-3-Hydroxypregn-16-en-20-one

생성물 1

HCID 86733309HCID 86733309, 화합물수율 89.4%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

3β-Hydroxy-5α-pregn-16-en-20-one (10 g.) in pyridine (50 ml.) was treated with toluene-p-sulphonyl chloride (10 g.), and the solution was stirred at room temperature overnight and then poured into dilute hydrochloric acid. The precipitate was extracted into chloroform, and the extract was washed with dilute hydrochloric acid and with water, dried over sodium sulphate and evaporated to an oil which crystallised on standing. Recrystallisation from ethyl acetate/petrol gave 3β-toluene-p-sulphonyloxy-5α-pregn-16-en-20-one (13.3g) as off-white prisms, m.p. 146°-148° , [α]D + 24.0°, λmax. (EtOH) 226.5 nm (ε 18,600), 240 nm (infl.) (ε 9550), 272.5 nm (ε 518).

후처리

  1. extractionThe precipitate was extracted into chloroform
  2. washthe extract was washed with dilute hydrochloric acid and with water
  3. dry with materialdried over sodium sulphate
  4. customevaporated to an oil which
  5. customcrystallised
  6. customRecrystallisation from ethyl acetate/petrol

출처 및 근거

ORD 기록
ord-f6c26d8628ad4f6eb18ed8a7cce8189e
출처 데이터셋
uspto-grants-1976_04
특허 번호
US03952031

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