Di-para-toluoyl-L-tartaric acid → (-)-(2R,3S)-2-Amino-3-hydroxy-3-pyridin-4-yl-1-pyrrolidin-1-yl-propan-1-one di-p-toluoyl-L-tartrate

HRID 593269

Reaction equation

HRID 593269 reaction equation
Cl.Cl.[NH2:3][CH:4]([CH:12]([OH:19])[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)[C:5]([N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6].[C:20]1([CH3:47])[CH:25]=[CH:24][C:23]([C:26]([C@@:28]([C:44]([OH:46])=[O:45])([OH:43])[C@@:29]([C:34]([C:36]2[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=2)=[O:35])([OH:33])[C:30]([OH:32])=[O:31])=[O:27])=[CH:22][CH:21]=1>>[C:20]1([CH3:47])[CH:25]=[CH:24][C:23]([C:26]([C@@:28]([C:44]([OH:46])=[O:45])([OH:43])[C@@:29]([C:34]([C:36]2[CH:37]=[CH:38][C:39]([CH3:42])=[CH:40][CH:41]=2)=[O:35])([OH:33])[C:30]([OH:32])=[O:31])=[O:27])=[CH:22][CH:21]=1.[NH2:3][C@H:4]([C@@H:12]([OH:19])[C:13]1[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=1)[C:5]([N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6]

Participants

3

Reactant 2

HCID 29414711Di-para-toluoyl-L-tartaric acidHCID 66901564HCID 66901564, compound

Product 1

HCID 131734560(-)-(2R,3S)-2-Amino-3-hydroxy-3-pyridin-4-yl-1-pyrrolidin-1-yl-propan-1-one di-p-toluoyl-L-tartrate

Procedure

Resolving the (+/−)-DL-threo-2-amino-3-hydroxy-3-pyridin-4-yl-1-pyrrolidin-1-yl-propan-1-one dihydrochloride in the presence of Di-p-toluoyl-L-tartaric acid to produce (−)-(2R,3S)-2-Amino-3-hydroxy-3-pyridin-4-yl-1-pyrrolidin-1-yl-propan-1-one di-p-toluoyl-L-tartrate;

Sources & evidence

ORD record
ord-eba4f28d77bf40d69acf3a35ce0bb324
Source dataset
uspto-grants-2016_01
Patent number
US09242935B2

Linked notes

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