Hydrochloric Acid → Travoprost

HRID 402868

반응식

HRID 402868 반응식
[Si]([O:8][C@@H:9]([CH2:38][O:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([C:46]([F:49])([F:48])[F:47])[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.Cl.C([O-])(O)=O.[Na+]>C(O)(C)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][O:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([C:46]([F:47])([F:48])[F:49])[CH:41]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 67226385Isopropyl (Z)-7-((1R,2R,3R,5S)-2-((3R,E)-3-(tert-butyldimethylsilyloxy)-4-(3-(trifluoromethyl)-phenoxy)-but-1-enyl)-3-(tert-butyldimethylsilyloxy)-5-hydroxy-cyclopentyl)-hept-5-enoate

생성물 1

HCID 5282226Travoprost수율 99%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

A mixture of crude compound (11a) (10 g), 2N HCl (37 mL) and isopropanol (IPA) (100 mL) was stirred. The reaction solution was neutralized with saturated aqueous NaHCO3 and extracted twice with EtOAc (80 mL each), once with saturated aqueous NaCl (80 mL) and then the organic layer was concentrated under reduced pressure. The product was purified twice by column chromatography using mixtures of EtOAc and n-heptane to afford Travoprost (HPLC>99.0%).

후처리

  1. extractionextracted twice with EtOAc (80 mL each), once with saturated aqueous NaCl (80 mL)
  2. concentrationthe organic layer was concentrated under reduced pressure
  3. customThe product was purified twice by column chromatography

출처 및 근거

ORD 기록
ord-4a676bb44e4c4473b3b3c19a11b1bfec
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742143B2

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