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Dimethylformamide → Fluocortin

HRID 2072191
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HRID 2072191 반응식
[F:1][C@@H:2]1[C:22]2[C@:17]([CH3:24])([CH:18]=[CH:19][C:20](=[O:23])[CH:21]=2)[C@@H:16]2[C@H:4]([C@H:5]3[C@:13]([CH3:26])([CH2:14][C@@H:15]2[OH:25])[C@@H:8]([C:9](=[O:12])[CH:10]=[O:11])[C@H:7]([CH3:27])[CH2:6]3)[CH2:3]1.CN(C)C=[O:31].FCCO.[C-]#N.[K+]>[O-2].[Mn+4].[O-2].C(O)(=O)C>[F:1][C@@H:2]1[C:22]2[C@:17]([CH3:24])([CH:18]=[CH:19][C:20](=[O:23])[CH:21]=2)[C@@H:16]2[C@H:4]([C@H:5]3[C@:13]([CH3:26])([CH2:14][C@@H:15]2[OH:25])[C@@H:8]([C:9](=[O:12])[C:10]([OH:31])=[O:11])[C@H:7]([CH3:27])[CH2:6]3)[CH2:3]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 9032Potassium CyanideHCID 97372-FluoroethanolHCID 86735083HCID 86735083, 화합물

생성물 1

HCID 22875828Fluocortin

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매
HCID 176
Acetic Acid
용매

실험 절차

1.4 g. of 6α-fluoro-11β-hydroxy-3,20-dioxo-16α-methyl-1,4-pregnadien-21-al is dissolved in 14 ml. of dimethylformamide and combined with 5 ml. of 2-fluoroethanol, 1.4 ml. of concentrated acetic acid, 2.8 g. of active manganese (IV) oxide, and 225 mg. of potassium cyanide. The reaction mixture is agitated for 10 minutes at room temperature and then filtered off from the manganese (IV) oxide. The filtrate is poured into water and extracted with dichloromethane. The organic phase is washed with water, dried with sodium sulfate, and concentrated under vacuum. The residue is chromatographed on silica gel. With 31-33% acetone-hexane, after recrystallization from acetone/hexane, 630 mg. of the 2-fluoroethyl ester of 6α-fluoro-11β-hydroxy-3,20-dioxo-16α-methyl-1,4-pregnadien-21-oic acid is obtained; m.p. 188.0° C. [α]D25 = +141° (chloroform). UV: ε242 = 16,900 (methanol)

후처리

  1. filtrationfiltered off from the manganese (IV) oxide
  2. additionThe filtrate is poured into water
  3. extractionextracted with dichloromethane
  4. washThe organic phase is washed with water
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue is chromatographed on silica gel
  8. customWith 31-33% acetone-hexane, after recrystallization from acetone/hexane, 630 mg

출처 및 근거

ORD 기록
ord-2c0946b893fa45b2a8541cfbdd9ce654
출처 데이터셋
uspto-grants-1977_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04049804

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