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

HRID 1394811

Reaktionsgleichung

Reaktionsgleichung von HRID 1394811
[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-tartrate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

In a preferred embodiment, (RS)-N-benzyl-N-methyl-2-phenylglycinamide is treated with di(o-toluoyl)-L-tartaric acid in methanol at 20° C. The precipitated salt is filtered and washed with methanol, then dried providing (S)-N-benzyl-N-methyl-2-phenylglycinamide di(o-toluoyl)-L-tartrate with 92.7% d.e. (chiral HPLC). This material is reslurried in hot methanol, filtered, washed and dried to providing (S)-N-benzyl-N-methyl-2-phenylglycinamide di(o-toluoyl)-L-tartrate with 99% d.e. (37% overall yield).

Aufarbeitung

  1. filtrationThe precipitated salt is filtered
  2. washwashed with methanol
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-035abe70225f44788d4435d7caded27a
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07348355B2

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