Sodium Hydroxide → HCID 59166768, Verbindung

HRID 1442960Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1442960
CC[O:3][C:4]([C@@H:6]1[CH2:10][C@H:9]([S:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)[CH2:8][N:7]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:5].[OH-].[Na+]>CO>[C:22]([O:21][C:19]([N:7]1[CH2:8][C@@H:9]([S:11][C:12]2[CH:13]=[CH:14][C:15]([Br:18])=[CH:16][CH:17]=2)[CH2:10][C@H:6]1[C:4]([OH:5])=[O:3])=[O:20])([CH3:25])([CH3:23])[CH3:24]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 59166754HCID 59166754, Verbindung

Produkt 1

HCID 59166768HCID 59166768, VerbindungAusbeute 107,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

(2S,4S)-4-(4-Bromo-phenylsulfanyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (Preparation 5, 120 mg, 0.30 mmol) was dissolved in MeOH (6 ml) and 2M sodium hydroxide was added (0.83 ml, 1.66 mmol). The solution was stirred for 14 h, concentrated and added to 0.5M HCl (50 ml). The aqueous was extracted with CH2Cl2 (50 ml) which was dried (magnesium sulphate) and concentrated. Flash column chromatography (eluting first with CH2Cl2 and then with 95% CH2Cl2/MeOH) gave the acid as a clear liquid (130 mg, 48%).

Aufarbeitung

  1. concentrationconcentrated
  2. additionadded to 0.5M HCl (50 ml)
  3. extractionThe aqueous was extracted with CH2Cl2 (50 ml) which
  4. dry with materialwas dried (magnesium sulphate)
  5. concentrationconcentrated
  6. washFlash column chromatography (eluting first with CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-e5ee404a7d824fdc9525811b9bc79ee1
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07659305B2

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