Triamcinolone → 9-Fluoro-11beta,16alpha,17,21-tetrahydroxypregn-4-ene-3,20-dione

HRID 1585479노트

반응식

HRID 1585479 반응식
[CH3:1][C@@:2]12[C@@:10]([OH:15])([C:11]([CH2:13][OH:14])=[O:12])[C@H:9]([OH:16])[CH2:8][C@H:7]1[C@@H:6]1[CH2:17][CH2:18][C:19]3[C@@:25]([CH3:26])([C@@:5]1([F:27])[C@@H:4]([OH:28])[CH2:3]2)[CH:24]=[CH:23][C:21](=[O:22])[CH:20]=3>C1(C)C=CC=CC=1.C(O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[CH3:26][C@@:25]12[C@@:5]3([F:27])[C@@H:4]([OH:28])[CH2:3][C@:2]4([CH3:1])[C@@:10]([OH:15])([C:11]([CH2:13][OH:14])=[O:12])[C@H:9]([OH:16])[CH2:8][C@H:7]4[C@@H:6]3[CH2:17][CH2:18][C:19]1=[CH:20][C:21](=[O:22])[CH2:23][CH2:24]2

참가 물질

5

반응물 1

HCID 31307Triamcinolone

생성물 1

HCID 2287859-Fluoro-11beta,16alpha,17,21-tetrahydroxypregn-4-ene-3,20-dione

시약·촉매·용매 3

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)촉매HCID 702Ethanol용매HCID 1140Toluene용매

실험 절차

A suspension of 3.0 g of tris(triphenylphosphine)rhodium chloride in 1000 ml of degassed toluene was hydrogenated for 45 min at room temperature and atmospheric pressure. A solution of 5.0 g of triamcinolone in 500 ml of absolute ethanol was added and the hydrogenation was continued for 48 h. The reaction mixture was evaporated to dryness and suspended in 50 ml of methylene chloride. After filtration the solid phase was repeatedly washed with small portions of methylene chloride and yielded after drying 4.4 g of 9α-fluoro-11β,16α,17α,21-tetrahydroxypregn-4-ene-3,20-dione. Molecular weight 396 (calc. 396.5).

후처리

  1. waitthe hydrogenation was continued for 48 h
  2. customThe reaction mixture was evaporated to dryness
  3. filtrationAfter filtration the solid phase
  4. washwas repeatedly washed with small portions of methylene chloride
  5. customyielded
  6. dry with materialafter drying 4.4 g of 9α-fluoro-11β,16α,17α,21-tetrahydroxypregn-4-ene-3,20-dione

출처 및 근거

ORD 기록
ord-12d5e8139c61486b81b47158dbc0c6ac
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05939409

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