Butanol acetic acid water → (S)-1-(Diphenylacetyl)piperazine-2-carboxylic acid acetate salt

HRID 2226596Notes

Reaction equation

HRID 2226596 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:31])[CH: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)[C@H:13]([C:32]([OH:34])=[O:33])[CH2:12]1)=O)C1C=CC=CC=1.C(O)CCC.C(O)(=O)C.O>CO.[Pd]>[C:32]([OH:34])(=[O:33])[CH3:13].[C:25]1([CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:17]([N:14]2[CH2:15][CH2:16][NH:11][CH2:12][C@H:13]2[C:32]([OH:34])=[O:33])=[O:31])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 22056973Butanol acetic acid waterHCID 22850671(S)-4-(Benzyloxycarbonyl)-1-(diphenylacetyl)piperazine-2-carboxylic acid

Product 1

HCID 70074341(S)-1-(Diphenylacetyl)piperazine-2-carboxylic acid acetate salt

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 785 mg (1.71 mmole) of (S)-4-(benzyloxycarbonyl)-1-(diphenylacetyl)piperazine-2carboxylic acid (from Step A) in 25 ml of methanol was treated with 800 mg of 10% Pd/C and the mixture was hydrogenated at 40 psi at 25° C. with rocking for 4 hours. The mixture was filtered and the catalyst was washed with 4×30 ml of acetic acid. All organic phases were combined, concentrated in vacuo, redissolved in 100 ml of water and reconcentrated in vacuo to leave 404 mg (73%) of waxy solid which was homogeneous by TLC (4:1:1 n-butyl alcohol-acetic acid-water, Rf =0.55).

Workup

  1. filtrationThe mixture was filtered
  2. washthe catalyst was washed with 4×30 ml of acetic acid
  3. concentrationconcentrated in vacuo
  4. dissolutionredissolved in 100 ml of water
  5. customto leave 404 mg (73%) of waxy solid which

Sources & evidence

ORD record
ord-fceecc4d12aa425c9eef832497ec027a
Source dataset
uspto-grants-1994_09
Patent number
US05348955

Reaction notes

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