2-Benzylidene-3-(cis-hexahydro-2-isoindolinylcarbonyl)propionic acid → Mitiglinide

HRID 2261532Notes

Reaction equation

HRID 2261532 reaction equation
C1(OC(N2C[C@@H](P(C3C=CC=CC=3)C3C=CC=CC=3)C[C@H]2CP(C2C=CC=CC=2)C2C=CC=CC=2)=O)C=CC=CC=1.[CH:42](=[C:49]([CH2:53][C:54]([N:56]1[CH2:64][C@H:63]2[C@H:58]([CH2:59][CH2:60][CH2:61][CH2:62]2)[CH2:57]1)=[O:55])[C:50]([OH:52])=[O:51])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>>[CH:46]1[CH:45]=[CH:44][C:43]([CH2:42][C@H:49]([C:50]([OH:52])=[O:51])[CH2:53][C:54]([N:56]2[CH2:57][C@H:58]3[C@H:63]([CH2:62][CH2:61][CH2:60][CH2:59]3)[CH2:64]2)=[O:55])=[CH:48][CH:47]=1

Participants

3

Reactant 2

HCID 545718482-Benzylidene-3-(cis-hexahydro-2-isoindolinylcarbonyl)propionic acidHCID 86627672(2S,4S)-N-phenyloxycarbonyl-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidine

Product 1

HCID 121891Mitiglinide

Procedure

The preparation was carried out in the same manner as in Example 1, except that 3.02 mg of (2S,4S)-N-phenyloxycarbonyl-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidine (PPPM) was used instead of 3.02 mg of PCPPM of Example 1. After the reaction, the residual ratio of 2-benzylidene-3-(cis-hexahydro-2-isoindolinylcarbonyl)propionic acid was 9.74%, and the optical purity of mitiglinide thus obtained was 94.5% e.e.

Workup

  1. customAfter the reaction

Sources & evidence

ORD record
ord-d9a9ed885def4d6aa0e19770fe17ec7f
Source dataset
uspto-grants-2010_12
Patent number
US07847107B2

Reaction notes

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