Lithium Hydroxide → [(1-Biphenyl-4-yl-ethyl)-tert-butoxycarbonyl-amino]-acetic acid

HRID 1178158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1178158
[Li+].[OH-].C[O:4][C:5](=[O:29])[CH2:6][N:7]([CH:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:19][CH:18]=1)[CH3:16])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]>C1COCC1.CO.O>[C:20]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:19]=[CH:18][C:17]([CH:15]([N:7]([CH2:6][C:5]([OH:29])=[O:4])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH3:16])=[CH:22][CH:21]=1

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 59559672[(1-Biphenyl-4-yl-ethyl)-tert-butoxycarbonyl-amino]-acetic acid methyl ester

Produkt 1

HCID 59559653[(1-Biphenyl-4-yl-ethyl)-tert-butoxycarbonyl-amino]-acetic acidAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

LiOH (140 mg, 3.3 mmol) was added to a stirred solution of [(1-biphenyl-4-yl-ethyl)-tert-butoxycarbonyl-amino]-acetic acid methyl ester (202 mg, 0.54 mmol) in THF:MeOH:H2O (3:1:1, 10 mL), and the resulting mixture was stirred at room temperature for 12 hrs. The reaction mixture was concentrated under reduced pressure. Cold water was then added, the product was acidified with aqueous citric acid solution and then extracted with EtOAc. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to afford 190 mg (97.9% yield) of [(1-biphenyl-4-yl-ethyl)-tert-butoxycarbonyl-amino]-acetic acid.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionCold water was then added
  3. extractionextracted with EtOAc
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bfb1c9103d1f4b3ca43ed362a6fb5848
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842696B2

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