2,3-Dihydroxybutanedioic Acid → Butanedioic acid, 2,3-bis(benzoyloxy)-, (2S,3S)-

HRID 1866780Notes

Reaction equation

HRID 1866780 reaction equation
[C:1]([OH:10])(=[O:9])[CH:2]([CH:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3].C(O)(=O)[CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[OH:13].C[O:23][C:24](C(F)(F)F)(C(O)=O)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>>[CH:28]1[CH:27]=[CH:26][C:25]([C:24]([O:3][C@H:2]([C:1]([OH:10])=[O:9])[C@H:4]([O:5][C:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:13])[C:6]([OH:8])=[O:7])=[O:23])=[CH:30][CH:29]=1

Participants

5

Reactant 4

HCID 8752,3-Dihydroxybutanedioic AcidHCID 1292Mandelic AcidHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 86531Mosher's acid

Product 1

HCID 1550213Butanedioic acid, 2,3-bis(benzoyloxy)-, (2S,3S)-

Procedure

producing a chiral salt of III′ by treating the compound of formula (III′) with a chiral resolving agent (e.g., tartaric acid, mandelic acid, Mosher's acid, camphor sulphonic acid, etc., or, preferably, (+)-2,3-dibenzoyl-D-tartaric acid to yield a chiral salt (e.g., (3S,4R)-enantiomer (+)-2,3-dibenzoyl-D-tartrate salt when (+)-2,3-dibenzoyl-D-tartaric acid is the chiral resolving agent)) and isolating the cis isomer of III′ thereby produced;

Sources & evidence

ORD record
ord-ec8f230932054f468436249c7e37b559
Source dataset
uspto-grants-2009_12
Patent number
US07629466B2

Reaction notes

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