2,3-Dihydroxybutanedioic Acid → 5-benzyl-5-[2-((2S,4S)-2-cyano-4-fluoro-pyrrolidin-1-yl)-2-oxo-ethylamino]-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide tartrate

HRID 1961597Notes

Reaction equation

HRID 1961597 reaction equation
[CH3:1][N:2]([CH3:32])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([NH:13][CH2:14][C:15]([N:17]3[CH2:21][C@@H:20]([F:22])[CH2:19][C@H:18]3[C:23]#[N:24])=[O:16])[CH2:12][CH:7]2[CH2:6]1)=[O:4].[C:33]([OH:42])(=[O:41])[CH:34]([CH:36]([C:38]([OH:40])=[O:39])[OH:37])[OH:35]>ClCCl.CC(C)=O>[C:38]([CH:36]([CH:34]([C:33]([OH:42])=[O:41])[OH:35])[OH:37])([OH:40])=[O:39].[CH3:32][N:2]([CH3:1])[C:3]([N:5]1[CH2:6][CH:7]2[CH2:12][C:11]([CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)([NH:13][CH2:14][C:15]([N:17]3[CH2:21][C@@H:20]([F:22])[CH2:19][C@H:18]3[C:23]#[N:24])=[O:16])[CH2:10][CH:8]2[CH2:9]1)=[O:4]

Participants

5

Reactant 2

HCID 8752,3-Dihydroxybutanedioic AcidHCID 687750445-benzyl-5-[2-((2S,4S)-2-cyano-4-fluoro-pyrrolidin-1-yl)-2-oxo-ethylamino]-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide

Product 1

HCID 687756035-benzyl-5-[2-((2S,4S)-2-cyano-4-fluoro-pyrrolidin-1-yl)-2-oxo-ethylamino]-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide tartrateYield 68%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

5-Benzyl-5-[2-((2S,4S)-2-cyano-4-fluoro-pyrrolidin-1-yl)-2-oxo-ethylamino]-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 14g (87 mg, 0.197 mmol) was dissolved in 3 mL of dichloromethane with stirring followed by dropwise addition of a solution of 3 mL of tartaric acid in acetone. The reaction mixture was reacted at room temperature for 30 minutes and concentrated. The resulting residue was recrystallized from a solvent mixture of ethyl acetate/acetone to obtain the title compound 5-benzyl-5-[2-((2S,4S)-2-cyano-4-fluoro-pyrrolidin-1-yl)-2-oxo-ethylamino]-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide tartrate 14 (80 mg, yield 68%) as a white solid.

Workup

  1. customThe reaction mixture was reacted at room temperature for 30 minutes
  2. concentrationconcentrated
  3. customThe resulting residue was recrystallized from a solvent mixture of ethyl acetate/acetone

Sources & evidence

ORD record
ord-30e0a65c3cea4bd980584a402c7d24e5
Source dataset
uspto-grants-2013_04
Patent number
US08415349B2

Reaction notes

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