(RS)-N-benzyl-N-methyl-2-phenylglycinamide → (S)-N-benzyl-N-methyl-2-phenylglycinamide di(o-toluoyl)-L-tartrate

HRID 498875

Reaktionsgleichung

Reaktionsgleichung von HRID 498875
[CH2:1]([N:8]([CH3:19])[C:9](=[O:18])[CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]1([CH3:47])[C:21]([C:26]([C@@:28]([C:44]([OH:46])=[O:45])([OH:43])[C@@:29]([C:34]([C:36]2[C:37]([CH3:42])=[CH:38][CH:39]=[CH:40][CH:41]=2)=[O:35])([OH:33])[C:30]([OH:32])=[O:31])=[O:27])=[CH:22][CH:23]=[CH:24][CH:25]=1>CO>[C:20]1([CH3:47])[C:21]([C:26]([C@@:28]([C:44]([OH:46])=[O:45])([OH:43])[C@@:29]([C:34]([C:36]2[C:37]([CH3:42])=[CH:38][CH:39]=[CH:40][CH:41]=2)=[O:35])([OH:33])[C:30]([OH:32])=[O:31])=[O:27])=[CH:22][CH:23]=[CH:24][CH:25]=1.[CH2:1]([N:8]([CH3:19])[C:9](=[O:18])[C@H:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH2:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 22262712(RS)-N-benzyl-N-methyl-2-phenylglycinamideHCID 129746773Ditoluoyl-l-tartaric acid

Produkt 1

HCID 131724412(S)-N-benzyl-N-methyl-2-phenylglycinamide di(o-toluoyl)-L-tartrateAusbeute 46,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

In a preferred embodiment, (RS)-N-benzyl-N-methyl-2-phenylglycinamide (10.0 g) was treated with di(o-toluoyl)-L-tartaric acid (15.2 g) in methanol (167 mL) at 20° C. The precipitated the salt was filtered and washed with methanol, then dried providing (S)-N-benzyl-N-methyl-2-phenylglycinamide di(o-toluoyl)-L-tartrate (11.73 g, 46.6%) with 92.7% d.e. (chiral HPLC). This material (1.00 g) was reslurried in hot methanol (8.8 ml) to provide (S)-N-benzyl-N-methyl-2-phenylglycinamide di(o-toluoyl)-L-tartrate with 99% d.e. (0.79 g, 79% recovery) after filtration, washing and drying. The tartrate salts formed as described maybe broken to provide the free amine of formula C, i.e. (S)-N-benzyl-N-methyl-2-phenylglycinamide, which may be advantageously purified by the formation of a salt with an achiral acid in the presence of appropriate solvents, e.g. precipitation of (S)-N-benzyl-N-methyl-2-phenylglycinamide hydrochloride from mixtures of propan-2-ol and tert-butyl methyl ether as described.

Aufarbeitung

  1. customThe precipitated the salt
  2. filtrationwas filtered
  3. washwashed with methanol
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-beda1220d356461b9ebd16d724ccb558
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06949572B2

Verknüpfte Notizen

Wird geladen…