DL-threo-Ritalinic acid → HCID 131734963, compound

HRID 922161Notes

Reaction equation

HRID 922161 reaction equation
[CH2:1]1[CH2:6][C@H:5]([C@H:7]([C:14]([OH:16])=[O:15])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[NH:4][CH2:3][CH2:2]1.[C:17]([C@:25]([C:40]([OH:42])=[O:41])([OH:39])[C@:26]([C:31](=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([OH:30])[C:27]([OH:29])=[O:28])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CO.O>[CH2:1]1[CH2:6][C@H:5]([C@H:7]([C:14]([OH:16])=[O:15])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:4][CH2:3][CH2:2]1.[C:31]([C:26]([C:27]([OH:29])=[O:28])([OH:30])[C:25]([C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([OH:39])[C:40]([OH:42])=[O:41])(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 10922012DL-threo-Ritalinic acidHCID 12362977Di-benzoyl-d-tartaric acid

Product 1

HCID 131734963HCID 131734963, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

US 2011/0130569 discloses a process for the preparation of the d-threo-ritalinic acid. dl-threo-ritalinic acid treated with (+)-dibenzoyl-D-tartaric acid as resolving agent in large volume of solvents mixture of methanol/water to get d-threo-ritalinic acid-dibenzoyl tartaric acid salt. Thus obtained salt treated with 35% hydrochloric acid in mixture of toluene and water, concentrated under vacuum and isolated by treating with acetone. The volume of resolution solvent used herein is quite higher.

Sources & evidence

ORD record
ord-64de72ed257142bea8b0ee1569ba13f8
Source dataset
uspto-grants-2016_03
Patent number
US09278928B2

Reaction notes

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