4-[(S)-2-Benzyloxycarbonylamino-3-(2,2-dimethyl-[1,3]dioxolan-4-yl)-propionyl]-piperazine-1-carboxylic acid ethyl ester → 4-[(S)-2-Amino-3-(2,2-dimethyl-[1,3]dioxolan-4-yl)-propionyl]-piperazine-1-carboxylic acid ethyl ester

HRID 1970498Notes

Reaction equation

HRID 1970498 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:33])[C@@H:13]([NH:22]C(OCC2C=CC=CC=2)=O)[CH2:14][CH:15]2[CH2:19][O:18][C:17]([CH3:21])([CH3:20])[O:16]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([C:12](=[O:33])[C@@H:13]([NH2:22])[CH2:14][CH:15]2[CH2:19][O:18][C:17]([CH3:20])([CH3:21])[O:16]2)[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 668547494-[(S)-2-Benzyloxycarbonylamino-3-(2,2-dimethyl-[1,3]dioxolan-4-yl)-propionyl]-piperazine-1-carboxylic acid ethyl ester

Product 1

HCID 668561374-[(S)-2-Amino-3-(2,2-dimethyl-[1,3]dioxolan-4-yl)-propionyl]-piperazine-1-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 612 mg 4-[(S)-2-Benzyloxycarbonylamino-3-(2,2-dimethyl-[1,3]dioxolan-4-yl)-propionyl]-piperazine-1-carboxylic acid ethyl ester in 15 ml ethyl acetate were added 200 mg Pd/C (10%) and the suspension stirred under an atmosphere of hydrogen (1 bar) for 12 h. The reaction mixture was filtered over a plug of Celite, washed with ethyl acetate, concentrated and the crude product used without further purification. Yield: 344 mg.

Workup

  1. filtrationThe reaction mixture was filtered over a plug of Celite
  2. washwashed with ethyl acetate
  3. concentrationconcentrated
  4. customthe crude product used without further purification

Sources & evidence

ORD record
ord-e0abdd8f3daa4d1490b14bda25a5a350
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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