2,3-Dihydroxybutanedioic Acid → HCID 68777215, compound

HRID 1873546Notes

Reaction equation

HRID 1873546 reaction equation
[CH3:1][N:2]([CH3:31])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=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:32]([OH:41])(=[O:40])[CH:33]([CH:35]([C:37]([OH:39])=[O:38])[OH:36])[OH:34].CCCCCC>C(OCC)(=O)C.CC(C)=O>[C:37]([CH:35]([CH:33]([C:32]([OH:41])=[O:40])[OH:34])[OH:36])([OH:39])=[O:38].[CH3:31][N:2]([CH3:1])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11]([CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=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 68777216HCID 68777216, compound

Product 1

HCID 68777215HCID 68777215, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Benzyl-5-[2-((S)-2-cyano-pyrrolidin-1-yl)-2-oxo-ethylamino]-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 17a (56 mg, 0.132 mmol) was dissolved in 1 mL of ethyl acetate with stirring followed by addition of a solution of 1 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-benzyl-5-[2-((S)-2-cyano-pyrrolidin-1-yl)-2-oxo-ethylamino]-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide tartrate 17 (50 mg, yield 67%) as a white solid.

Workup

  1. stirringThe reaction mixture was stirred for 30 minutes
  2. customresulting in the formation of a white precipitate
  3. stirringstirred again
  4. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-0ba861a14a2542b5b027be6a307f3ebd
Source dataset
uspto-grants-2012_11
Patent number
US08304411B2

Reaction notes

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