Trifluoroacetic acid → 1-[(4-Hydroxy-pyrrolidine-2-carbonyl)-amino]-2-vinyl-cyclopropanecarboxylic acid ethyl ester

HRID 1445420Notes

Reaction equation

HRID 1445420 reaction equation
C(OC([N:8]1[CH2:12][CH:11]([OH:13])[CH2:10][CH:9]1[C:14](=[O:26])[NH:15][C:16]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:18][CH:17]1[CH:19]=[CH2:20])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:24]([O:23][C:21]([C:16]1([NH:15][C:14]([CH:9]2[CH2:10][CH:11]([OH:13])[CH2:12][NH:8]2)=[O:26])[CH2:18][CH:17]1[CH:19]=[CH2:20])=[O:22])[CH3:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 235716032-(1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 668712681-[(4-Hydroxy-pyrrolidine-2-carbonyl)-amino]-2-vinyl-cyclopropanecarboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Compound 122 (10.5 g, 28.4 mmol) was dissolved in DCM (70 ml) and cooled to 0° C., TFA (35 ml) was added. After appr 1 h the solution was evaporated and neutralized with aqueous sodium carbonate and evaporated on silica. Purification of the crude product by column chromatography on silica (MeOH/DCM: 15/85) gave 9.7 g of still unpure compound title compound. This material was used in the next step.

Workup

  1. customthe solution was evaporated
  2. customevaporated on silica
  3. customPurification of the crude product by column chromatography on silica (MeOH/DCM: 15/85)

Sources & evidence

ORD record
ord-95aba84575fd4219bb7b922eeda5e7d6
Source dataset
uspto-grants-2010_02
Patent number
US07666834B2

Reaction notes

Loading…