HCID 66855276, compound → 4-[(S)-4-tert-Butoxycarbonyl-2-({5-[2-(3-carboxy-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-butyryl]-piperazine-1-carboxylic acid ethyl ester

HRID 1970482Notes

Reaction equation

HRID 1970482 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:56])[C@@H:13]([NH:23][C:24]([C:26]2[CH:30]=[C:29]([O:31][CH2:32][C:33]([N:35]3[CH2:39][CH2:38][CH:37]([C:40]([O:42]CC4C=CC=CC=4)=[O:41])[CH2:36]3)=[O:34])[N:28]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[N:27]=2)=[O:25])[CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[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:56])[C@@H:13]([NH:23][C:24]([C:26]2[CH:30]=[C:29]([O:31][CH2:32][C:33]([N:35]3[CH2:39][CH2:38][CH:37]([C:40]([OH:42])=[O:41])[CH2:36]3)=[O:34])[N:28]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[N:27]=2)=[O:25])[CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 66855276HCID 66855276, compound

Product 1

HCID 668547954-[(S)-4-tert-Butoxycarbonyl-2-({5-[2-(3-carboxy-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-butyryl]-piperazine-1-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2.32 g 4-[(S)-2-({5-[2-(3-benzyloxycarbonyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-4-tert-butoxycarbonyl-butyryl]-piperazine-1-carboxylic acid ethyl ester in 50 ml ethyl acetate was added 1.0 g Pd/C (10%) and the suspension stirred under an atmosphere of hydrogen (3 bar) for 24 h. The reaction mixture was filtrated over a plug of Celite, washed with ethyl acetate and concentrated.

Workup

  1. filtrationThe reaction mixture was filtrated over a plug of Celite
  2. washwashed with ethyl acetate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-03b00b0399d945779585400c283dae7a
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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