(2S,5S)-5-(2-benzylamino-2-carboxyethyl)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester → HCID 69643666, compound

HRID 10423Notes

Reaction equation

HRID 10423 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][CH:14]([NH:18]CC2C=CC=CC=2)[C:15]([OH:17])=[O:16])[CH2:11][CH2:10][C@H:9]1[C:26]([OH:28])=[O:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)(=O)C.[OH-].[OH-].[Pd+2]>[C:15]([OH:17])(=[O:16])[CH3:14].[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][CH:14]([NH2:18])[C:15]([OH:17])=[O:16])[CH2:11][CH2:10][C@H:9]1[C:26]([OH:28])=[O:27])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 69643721(2S,5S)-5-(2-benzylamino-2-carboxyethyl)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 69643666HCID 69643666, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

1600 mg of (2S,5S)-5-(2-benzylamino-2-carboxyethyl)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester were dissolved in 30 ml of acetic acid. 100 mg of 20% palladium hydroxide on activated carbon were added thereto, and the mixture was hydrogenated under an atmosphere of 1 bar of hydrogen for 1 h. Ar was then passed over the solution for 10 min. The catalyst was filtered off through kieselguhr and the filter cake was washed with 20 ml of acetic acid. The combined organic phases were concentrated in vacuo. The crude product was employed without further purification in the next reaction.

Workup

  1. filtrationThe catalyst was filtered off through kieselguhr
  2. washthe filter cake was washed with 20 ml of acetic acid
  3. concentrationThe combined organic phases were concentrated in vacuo
  4. customThe crude product was employed without further purification in the next reaction

Sources & evidence

ORD record
ord-0671b17e79594082bfe04925787d737d
Source dataset
uspto-grants-2006_08
Patent number
US07094800B2

Reaction notes

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