(2S,4R)-2-((1S 2R)1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert.butyl ester → (1S,2R)-1-[(2S,4R)-(4-Hydroxy-pyrrolidine-2-carbonyl)-amino]-2-vinyl-cyclopropanecarboxylic acid ethyl ester

HRID 1443443Notes

Reaction equation

HRID 1443443 reaction equation
C(OC([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14](=[O:26])[NH:15][C@@:16]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:18][C@@H:17]1[CH:19]=[CH2:20])=O)(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[CH2:24]([O:23][C:21]([C@:16]1([NH:15][C:14]([C@@H:9]2[CH2:10][C@@H:11]([OH:13])[CH2:12][NH:8]2)=[O:26])[CH2:18][C@@H:17]1[CH:19]=[CH2:20])=[O:22])[CH3:25]

Participants

4

Reactant 1

HCID 57563804(2S,4R)-2-((1S 2R)1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert.butyl ester

Product 1

HCID 68409004(1S,2R)-1-[(2S,4R)-(4-Hydroxy-pyrrolidine-2-carbonyl)-amino]-2-vinyl-cyclopropanecarboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 59 was kept in 30% trifluoroacetic acid in dichloromethane and 1% MeOH for 2 hrs before it was concentrated to dryness. The residue was re-dissolved in dichloromethane and during stirring 1N NaOH was added to pH 10-11. The organic layer was separated and concentrated which gave 1.6 g of the title compound. HPLC purity ca. 90% (M+H)+ 269.1.

Workup

  1. concentration1% MeOH for 2 hrs before it was concentrated to dryness
  2. dissolutionThe residue was re-dissolved in dichloromethane
  3. additionwas added to pH 10-11
  4. customThe organic layer was separated
  5. concentrationconcentrated which

Sources & evidence

ORD record
ord-97d62dd9abf44ba8a9e7f5b142af31a4
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

Loading…