Carbonate Ion → Arbaclofen Placarbil

HRID 558064Notes

Reaction equation

HRID 558064 reaction equation
C(=O)([O-])[O-].[C:5]([O:10][C@@H:11]([O:15][C:16]([O:18]C1CC(=O)NC1=O)=O)[CH:12]([CH3:14])[CH3:13])(=[O:9])[CH:6]([CH3:8])[CH3:7].[CH:26]1[C:31]([C@H:32]([CH2:37][NH2:38])[CH2:33][C:34]([OH:36])=[O:35])=[CH:30][CH:29]=[C:28]([Cl:39])[CH:27]=1>C(OC)(C)(C)C.O>[CH3:14][CH:12]([CH3:13])[C@@H:11]([O:10][C:5](=[O:9])[CH:6]([CH3:7])[CH3:8])[O:15][C:16]([NH:38][CH2:37][C@@H:32]([C:31]1[CH:26]=[CH:27][C:28]([Cl:39])=[CH:29][CH:30]=1)[CH2:33][C:34]([OH:36])=[O:35])=[O:18]

Participants

6

Reactant 3

HCID 19660Carbonate IonHCID 44602ArbaclofenHCID 68997310{[(1S)-isobutanoyloxyisobutoxy]carbonyloxy} succinimide

Product 1

HCID 11281011Arbaclofen Placarbil

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A 20-L pilot plant equipped with a mechanical stirrer and a nitrogen inlet was charged with NHS-carbonate, 1-S-[[[(isobutyryloxy)isobutyroxy]carbonyl]oxy]-2,5-pyrrolidinedione (20b), 1.31 kg, 4.7 mol) and (R)-baclofen (431 g; overall 1.2 eq. of R-baclofen) in a mixture of methyl tert-butyl ether (MTBE) and water (3:1; 10 L). The resulting suspension is stirred for 24 hours at room temperature.

Workup

  1. customA 20-L pilot plant equipped with a mechanical stirrer and a nitrogen inlet

Sources & evidence

ORD record
ord-b362f98e6fa6415ca804467edc06d6ae
Source dataset
uspto-grants-2011_11
Patent number
US08062870B2

Reaction notes

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