Sodium Bicarbonate → 17-phenyl-trinor-PGF2alpha isopropyl ester

HRID 2090544노트

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HRID 2090544 반응식
[Si]([O:8][C@@H:9]([CH2:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)/[CH:10]=[CH:11]/[C@H:12]1[C@H:16]([O:17][Si](C(C)(C)C)(C)C)[CH2:15][C@H:14]([OH:25])[C@@H:13]1[CH2:26]/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][C:32]([O:34][CH:35]([CH3:37])[CH3:36])=[O:33])(C(C)(C)C)(C)C.C([O-])(O)=O.[Na+]>CC(O)C>[OH:17][C@@H:16]1[CH2:15][C@H:14]([OH:25])[C@H:13]([CH2:26]/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][C:32]([O:34][CH:35]([CH3:37])[CH3:36])=[O:33])[C@H:12]1/[CH:11]=[CH:10]/[C@@H:9]([OH:8])[CH2:38][CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

참가 물질

4

반응물 2

HCID 516892Sodium BicarbonateHCID 67226382HCID 67226382, 화합물

생성물 1

HCID 528310717-phenyl-trinor-PGF2alpha isopropyl ester수율 111%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

A solution of compound (11b) (60 g) prepared in EXAMPLE 20 and aqueous HF (2 N, 135 mL) in IPA (240 mL) was stirred. Saturated aqueous NaHCO3 (120 mL) was added and the mixture was extracted with EtOAc (600 mL). The separated aqueous layer was extracted with EtOAc (300 mL) and the combined organic layer was washed with saturated aqueous NaCl (300 mL), dried with Na2SO4, filtered, and the filter cake was washed with EtOAc (200 mL). The filtrate was concentrated to furnish 43.5 g of crude compound (11c) (84.3% HPLC purity, 84% yield) which was directly used without purification in EXAMPLE 22.

후처리

  1. extractionthe mixture was extracted with EtOAc (600 mL)
  2. extractionThe separated aqueous layer was extracted with EtOAc (300 mL)
  3. washthe combined organic layer was washed with saturated aqueous NaCl (300 mL)
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. washthe filter cake was washed with EtOAc (200 mL)
  7. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-b5971ff6791045a480a0f34ef7326589
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436194B2

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