Water → 4-tert-Butoxycarbonylamino-2-(3,4-dichlorophenyl)-butyric acid

HRID 1823924Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1823924
C[O:2][C:3](=[O:23])[CH:4]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1)[CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].O.[OH-].[Li+]>C1COCC1>[C:11]([O:10][C:8]([NH:7][CH2:6][CH2:5][CH:4]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1)[C:3]([OH:23])=[O:2])=[O:9])([CH3:14])([CH3:12])[CH3:13]

Komponenten

5

Edukt 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 235709514-Tert-butoxycarbonylamino-2-(3,4-dichlorophenyl)-butyric acid methyl ester

Produkt 1

HCID 221479534-tert-Butoxycarbonylamino-2-(3,4-dichlorophenyl)-butyric acidAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-tert-butoxycarbonylamino-2-(3,4-dichlorophenyl)-butyric acid methyl ester (12.3 g, 34 mmol) in THF (80 mL)/water (20 mL) was added lithium hydroxide (1.63 g, 68 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was concentrated and the residue diluted with water. After extraction with EtOAc, the aqueous phase was acidified to pH 5 by the addition of 2M aqueous hydrochloric acid solution. The aqueous phase was extracted with EtOAc and the extracts dried over magnesium sulfate. Concentration gave the title compound as a pale brown foam (11.54 g, 98%); 1H NMR (400 MHz, DMSO) δ 1.35 (9H, s), 1.74–1.81 (1H, m), 2.03–2.10 (1H, m), 2.81 (2H, m), 3.61 (1H, t), 6.86 (1H, m), 7.28 (1H, dd), 7.54 (1H, dd), 7.59 (1H, d), 12.60 (1H, brs); MS (ES−) m/e=346.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue diluted with water
  3. extractionAfter extraction with EtOAc
  4. additionthe aqueous phase was acidified to pH 5 by the addition of 2M aqueous hydrochloric acid solution
  5. extractionThe aqueous phase was extracted with EtOAc
  6. dry with materialthe extracts dried over magnesium sulfate
  7. concentrationConcentration

Quellen und Nachweise

ORD-Eintrag
ord-abcf6e0a239345a1bae17a3dd71407b6
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07041687B2

Notizen zur Reaktion

Wird geladen…