2,3-Dihydroxybutanedioic Acid → HCID 68775604, compound

HRID 1873553Notes

Reaction equation

HRID 1873553 reaction equation
[CH3:1][N:2]([CH3:26])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11]([NH:15][CH2:16][C:17]([N:19]3[CH2:23][CH2:22][CH2:21][C@H:20]3[C:24]#[N:25])=[O:18])([CH2:13][CH3:14])[CH2:12][CH:7]2[CH2:6]1)=[O:4].[C:27]([OH:36])(=[O:35])[CH:28]([CH:30]([C:32]([OH:34])=[O:33])[OH:31])[OH:29]>C(OCC)(=O)C.CC(C)=O>[C:32]([CH:30]([CH:28]([C:27]([OH:36])=[O:35])[OH:29])[OH:31])([OH:34])=[O:33].[CH3:26][N:2]([CH3:1])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11]([NH:15][CH2:16][C:17]([N:19]3[CH2:23][CH2:22][CH2:21][C@H:20]3[C:24]#[N:25])=[O:18])([CH2:13][CH3:14])[CH2:12][CH:7]2[CH2:6]1)=[O:4]

Participants

5

Reactant 2

HCID 8752,3-Dihydroxybutanedioic AcidHCID 68775605HCID 68775605, compound

Product 1

HCID 68775604HCID 68775604, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-[2-((S)-2-Cyano-pyrrolidin-1-yl)-2-oxo-ethylamino]-5-ethyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 19g (120 mg, 0.33 mmol) was dissolved in 1 mL of ethyl acetate followed by dropwise addition of a solution of 2 mL of tartaric acid (50 mg, 0.33 mmol) in acetone. The reaction mixture was stirred for 30 minutes and filtered to obtain the title compound 5-[2-((S)-2-cyano-pyrrolidin-1-yl)-2-oxo-ethylamino]-5-ethyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide tartrate 19 (160 mg, yield 94%) as a white solid.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-62b5fc1744b049b4a5dd619dfae9416c
Source dataset
uspto-grants-2012_11
Patent number
US08304411B2

Reaction notes

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