Acetic Acid → PGF1alpha

HRID 1283483

반응식

HRID 1283483 반응식
[BH4-].[Na+].[CH3:3][CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]([OH:27])/[CH:9]=[CH:10]/[C@@H:11]1[C@@H:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C:14](=[O:15])[CH2:13][C@H:12]1[OH:26].CC(C)=O.C(O)(=O)C>CO>[CH3:3][CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]([OH:27])/[CH:9]=[CH:10]/[C@@H:11]1[C@@H:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C@@H:14]([OH:15])[CH2:13][C@H:12]1[OH:26]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 180AcetoneHCID 4311764Sodium borohydrideHCID 5280723Alprostadil

생성물 1

HCID 5280939PGF1alpha

시약·촉매·용매 1

HCID 887Methanol용매3회

실험 절차

Refer to Chart E wherein E is --CH=CH--, R2 and R4 are methyl, V is ---(CH2)5 --, W is 1-pentyl, and ~ is either alpha or beta. A solution of sodium borohydride (0.6 g.) in 10 ml. of methanol at 0° C. is added to a solution of PGE1, methyl ester, 15-methyl ether (Example 5, 1.5 g.) in 60 ml. of methanol and the mixture is stirred at 0° C. for 30 minutes. Acetone (10 ml.) is added and the solution is made slightly acid with dilute acetic acid in methanol. The mixture is concentrated by evaporation under reduced pressure and the residue is taken up in dichloromethane. The resulting solution is washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue is chromatographed over silica gel wet-packed in 8% methanol in dichlormethane ad rinsed with 300 ml. of dichloromethane, eluting with 2-10% methanol-dichloromethane. Those fractions shown by TLC to contain PGF1α , methyl ester, 15-methyl ether free of starting material and impurities are combined and concentrated to yield the Formula -VI PGF1α -type title compound. Likewise, those fractions shown by TLC to contain PGF1β, methyl ester, 15-methyl ether are combined and concentrated to yield the Formula-VI PGF1β -type title compound.

후처리

  1. concentrationThe mixture is concentrated by evaporation under reduced pressure
  2. washThe resulting solution is washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue is chromatographed over silica gel wet-packed in 8% methanol in dichlormethane ad
  6. washrinsed with 300 ml
  7. washof dichloromethane, eluting with 2-10% methanol-dichloromethane
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f895040f04e54d15bc0ce025db2c38af
출처 데이터셋
uspto-grants-1976_08
특허 번호
US03975404

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