Alprostadil → Pga1

HRID 26304

반응식

HRID 26304 반응식
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:12](=[O:13])[CH2:11][C@H:10]1O>C(O)(=O)C.O>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:12](=[O:13])[CH:11]=[CH:10]1

참가 물질

3

반응물 1

HCID 5280723Alprostadil

생성물 1

HCID 5281912Pga1

시약·촉매·용매 1

HCID 21899381Acetic acid--water (1/1)용매

실험 절차

A 125 mg (0.3 mmol) portion of the prostaglandin E1 analogue of Example 3 (14-Phenyl-11α,15R-dihydroxy-9-oxoprost-10,13E-dien-1-oic acid) was stirred into 10 ml of acetic acid-water (2:1) at 50° C. under an inert atmosphere. Progress of the reaction was followed by thin layer chromatography. After 48 hours, the reaction mixture was extracted with ether. Ether layers obtained were combined and washed to neutrality with brine. Removal of the solvent yielded a yellow oil. The oil was azeotroped with toluene and chromatographed on 70 g SG-60, and eluted with benzene-ethanol (19:1) to yield 102 mg of the PGA1 analogue.

후처리

  1. extractionthe reaction mixture was extracted with ether
  2. customEther layers obtained
  3. washwashed
  4. customRemoval of the solvent
  5. customyielded a yellow oil
  6. customThe oil was azeotroped with toluene
  7. customchromatographed on 70 g SG-60
  8. washeluted with benzene-ethanol (19:1)

출처 및 근거

ORD 기록
ord-2c28d4190b6e46498a16bbc8b4c01369
출처 데이터셋
uspto-grants-1979_04
특허 번호
US04149007

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