HCID 18965153, compound → HCID 70074640, compound

HRID 486745Notes

Reaction equation

HRID 486745 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:31])[N:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:13]([C:32]([OH:34])=[O:33])[CH2:12]1)=O)C1C=CC=CC=1.[H][H]>CO.[Pd].C(O)(=O)C>[C:32]([OH:34])(=[O:33])[CH3:13].[C:25]1([N:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:17]([N:14]2[CH2:15][CH2:16][NH:11][CH2:12][CH:13]2[C:32]([OH:34])=[O:33])=[O:31])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 2

HCID 18965153HCID 18965153, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70074640HCID 70074640, compound

Reagents, catalysts & solvents 3

HCID 887MethanolCatalystHCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 109 mg. (0.24 mmol) of (±)-4-(benzyloxycarbonyl)-1-(diphenylcarbamoyl)piperazine-2-carboxylic acid (from Step A) in 3 ml of methanol containing 3 drops of acetic acid and 50 mg of 10% Pd/C was hydrogenated with rocking at 40 psi of hydrogen for 16 hours. The mixture was filtered through Celite and the solution was concentrated in vacuo to 66 mg (71%) of solid which was homogeneous by TLC (1:1:1:1 n-butyl alcohol acetic acid-water-ethyl acetate, Rf =0.70).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe solution was concentrated in vacuo to 66 mg (71%) of solid which

Sources & evidence

ORD record
ord-875bf2a9daba45fe884e616d2e7284dc
Source dataset
uspto-grants-1994_03
Patent number
US05292726

Reaction notes

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