2,3-Dihydroxybutanedioic Acid → 5-[2-((2S,4S)-2-cyano-4-fluoro-pyrrolidin-1-yl)-2-oxo-ethylamino]-N,N,5-trimethyl-hexahydro-cyclopenta[c]pyrrole-2-carboxamide tartrate

HRID 1873529Notes

Reaction equation

HRID 1873529 reaction equation
[C:1]([C@@H:3]1[CH2:7][C@H:6]([F:8])[CH2:5][N:4]1[C:9](=[O:26])[CH2:10][NH:11][C:12]1([CH3:25])[CH2:24][CH:15]2[CH2:16][N:17]([C:19]([N:21]([CH3:23])[CH3:22])=[O:20])[CH2:18][CH:14]2[CH2:13]1)#[N:2].[C:27]([OH:36])(=[O:35])[CH:28]([CH:30]([C:32]([OH:34])=[O:33])[OH:31])[OH:29]>ClCCl.CC(C)=O>[C:32]([CH:30]([CH:28]([C:27]([OH:36])=[O:35])[OH:29])[OH:31])([OH:34])=[O:33].[C:1]([C@@H:3]1[CH2:7][C@H:6]([F:8])[CH2:5][N:4]1[C:9](=[O:26])[CH2:10][NH:11][C:12]1([CH3:25])[CH2:13][CH:14]2[CH2:18][N:17]([C:19]([N:21]([CH3:22])[CH3:23])=[O:20])[CH2:16][CH:15]2[CH2:24]1)#[N:2]

Participants

5

Reactant 2

HCID 8752,3-Dihydroxybutanedioic AcidHCID 687768935-[2-((2S,4S)-2-cyano-4-fluoro-pyrrolidin-1-yl)-2-oxo-ethylamino]-N,N,5-trimethyl-hexahydro-cyclopenta[c]pyrrole-2(1H)-carboxamide

Product 1

HCID 687771195-[2-((2S,4S)-2-cyano-4-fluoro-pyrrolidin-1-yl)-2-oxo-ethylamino]-N,N,5-trimethyl-hexahydro-cyclopenta[c]pyrrole-2-carboxamide tartrateYield 82%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

5-[2-((2S,4S)-2-Cyano-4-fluoro-pyrrolidin-1-yl)-2-oxo-ethylamino]-N,N,5-trimethyl-hexahydro-cyclopenta[c]pyrrole-2(1H)-2-carboxamide 13h (0.16 g, 0.44 mmol) was dissolved in 5 mL of dichloromethane with stirring followed by dropwise addition of a solution of 5 mL of tartaric acid (65.6 mg, 0.44 mmol) in acetone. The reaction mixture was reacted for 30 minutes resulting in the formation of a white precipitate. The mixture was filtered and the filter cake was washed with acetone to obtain the title compound 5-[2-((2S,4S)-2-cyano-4-fluoro-pyrrolidin-1-yl)-2-oxo-ethylamino]-N,N,5-trimethyl-hexahydro-cyclopenta[c]pyrrole-2-carboxamide tartrate 13 (0.18 g, yield 82%) as a white solid.

Workup

  1. customThe reaction mixture was reacted for 30 minutes
  2. customresulting in the formation of a white precipitate
  3. filtrationThe mixture was filtered
  4. washthe filter cake was washed with acetone

Sources & evidence

ORD record
ord-e220082026f0482b8581d12b7c75ef81
Source dataset
uspto-grants-2012_11
Patent number
US08304411B2

Reaction notes

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