(S)-2-(4'-Ethoxycarbonyl-6-trifluoromethoxy-biphenyl-3-ylcarbamoyl)-azetidine-1-carboxylic acid tert-butyl ester → (S)-2-(4'-Carboxy-6-trifluoromethoxy-biphenyl-3-ylcarbamoyl)-azetidine-1-carboxylic acid tert-butyl ester

HRID 1678503Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1678503
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[C:12](=[O:36])[NH:13][C:14]1[CH:15]=[C:16]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([O:33]CC)=[O:32])=[CH:27][CH:26]=2)[C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:18][CH:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[OH-].[Na+]>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[C:12](=[O:36])[NH:13][C:14]1[CH:15]=[C:16]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([OH:33])=[O:32])=[CH:27][CH:26]=2)[C:17]([O:20][C:21]([F:24])([F:22])[F:23])=[CH:18][CH:19]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 1

HCID 67371803(S)-2-(4'-Ethoxycarbonyl-6-trifluoromethoxy-biphenyl-3-ylcarbamoyl)-azetidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 67374213(S)-2-(4'-Carboxy-6-trifluoromethoxy-biphenyl-3-ylcarbamoyl)-azetidine-1-carboxylic acid tert-butyl esterAusbeute 86,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A mixture of (S)-2-(4′-Ethoxycarbonyl-6-trifluoromethoxy-biphenyl-3-ylcarbamoyl)-azetidine-1-carboxylic acid tert-butyl ester (188 mg) in ethanol (15 ml) and sodium hydroxide (2M, 5 ml) was stirred at room temp for 18 h. The mixture was acidified and the ethanol evaporated. The residue was extracted with DCM and the dried extracts evaporated giving the crude acid as a pale orange gum (154 mg).

Aufarbeitung

  1. customthe ethanol evaporated
  2. extractionThe residue was extracted with DCM
  3. customthe dried extracts evaporated

Quellen und Nachweise

ORD-Eintrag
ord-893b779fdab64a8d871c77a8bbf0f825
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008303B2

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