2,3-Dihydroxybutanedioic Acid → HCID 68775040, compound

HRID 1961607Notes

Reaction equation

HRID 1961607 reaction equation
[CH3:1][N:2]([CH3:29])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11]([CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)([NH:13][CH2:14][C:15]([N:17]3[CH2:21][CH2:20][CH2:19][C@H:18]3[C:22]#[N:23])=[O:16])[CH2:12][CH:7]2[CH2:6]1)=[O:4].[C:30]([OH:39])(=[O:38])[CH:31]([CH:33]([C:35]([OH:37])=[O:36])[OH:34])[OH:32].CCCCCC>C(OCC)(=O)C.CC(C)=O>[C:35]([CH:33]([CH:31]([C:30]([OH:39])=[O:38])[OH:32])[OH:34])([OH:37])=[O:36].[CH3:1][N:2]([CH3:29])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11]([CH:24]3[CH2:25][CH2:26][CH2:27][CH2:28]3)([NH:13][CH2:14][C:15]([N:17]3[CH2:21][CH2:20][CH2:19][C@H:18]3[C:22]#[N:23])=[O:16])[CH2:12][CH:7]2[CH2:6]1)=[O:4]

Participants

6

Reactant 3

HCID 8752,3-Dihydroxybutanedioic AcidHCID 8058HexaneHCID 68775041HCID 68775041, compound

Product 1

HCID 68775040HCID 68775040, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Cyclopentyl-5-[2-((S)-2-cyano-pyrrolidin-1-yl)-2-oxo-ethylamino]-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 16g (102 mg, 0.254 mmol) was dissolved in 2 mL of ethyl acetate followed by addition of a solution of 3 mL of tartaric acid in acetone. The reaction mixture was stirred for 30 minutes resulting in the formation of a white precipitate followed by addition of n-hexane, and stirred again. The mixture was filtered to obtain the title compound 5-cyclopentyl-5-[2-((S)-2-cyano-pyrrolidin-1-yl)-2-oxo-ethylamino]-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide tartrate 16 (88 mg, yield 65%) as a white solid.

Workup

  1. customresulting in the formation of a white precipitate
  2. stirringstirred again
  3. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-503cdd826924435789bc5be47eb6df89
Source dataset
uspto-grants-2013_04
Patent number
US08415349B2

Reaction notes

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