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

HRID 402870ノート

反応式

HRID 402870 の反応式
[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

参加物

4

反応物 2

HCID 516892Sodium BicarbonateHCID 67226382HCID 67226382、化合物

生成物 1

HCID 528310717-phenyl-trinor-PGF2alpha isopropyl ester収率 111%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c06f9f077fa542b3b8817214d37a9632
出典データセット
uspto-grants-2014_06
特許番号
US08742143B2

反応ノート

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