Ammonia → Modafinil acid

HRID 873554

Reaction equation

HRID 873554 reaction equation
CC([NH2:9])C1C=CC=CC=1.C(OS(C(C1C=CC=CC=1)C1C=CC=CC=1)=O)(=O)C.[CH:29]([S:42]([CH2:44][C:45]([OH:47])=[O:46])=[O:43])([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.S(OC)(OC)(=O)=O.N>>[CH:33]1[CH:32]=[CH:31][C:30]([CH:29]([S+:42]([O-:43])[CH2:44][C:45]([NH2:9])=[O:47])[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:35][CH:34]=1.[CH:39]1[CH:40]=[CH:41][C:36]([CH:29]([S:42]([CH2:44][C:45]([OH:47])=[O:46])=[O:43])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6497Dimethyl SulfateHCID 3085267Modafinil acidHCID 68553371(-)-alpha-Methylbenzylamine (-)-benzhydrylsulphinyl acetate

Product 2

HCID 3085267Modafinil acidHCID 178514057HCID 178514057, compound

Procedure

The (−)-α-methylbenzylamine-(−)-benzhydrylsulphinyl acetate is then converted to (−)-benzhydrylsulphinylacetic acid by acid hydrolysis. The latter is esterified in the presence of dimethyl sulphate and then converted to amide in the presence of ammonia (gas). The (−) or l (laevorotatory) enantiomer of modafinil is obtained through this process with an overall yield of 5.7% in relation to the (±) modafinil acid, calculated on the basis of the yields corresponding to each stage.

Sources & evidence

ORD record
ord-121bbe4373a546a3896070a84e83898e
Source dataset
uspto-grants-2015_03
Patent number
US08975442B2

Linked notes

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