Ethylmorpholine → 4-((S)-4-tert-Butoxycarbonyl-2-{[5-(3,3-dimethyl-2-oxo-butoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-butyryl)-piperazine-1-carboxylic acid benzyl ester

HRID 1908648Notes

Reaction equation

HRID 1908648 reaction equation
[C:1]([O:5][C:6](=[O:35])[CH2:7][CH2:8][C@H:9]([NH:13][C:14]([C:16]1[CH:20]=[C:19]([O:21][CH2:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[N:18]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:17]=1)=[O:15])[C:10]([OH:12])=O)([CH3:4])([CH3:3])[CH3:2].[N:36]1([C:42]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[O:43])[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1.C(N1CCOCC1)C.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O>CN(C=O)C.C(OCC)(=O)C>[CH2:45]([O:44][C:42]([N:36]1[CH2:41][CH2:40][N:39]([C:10](=[O:12])[C@@H:9]([NH:13][C:14]([C:16]2[CH:20]=[C:19]([O:21][CH2:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[N:18]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:17]=2)=[O:15])[CH2:8][CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:35])[CH2:38][CH2:37]1)=[O:43])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

7

Reactant 4

HCID 7525EthylmorpholineHCID 643495Benzyl piperazine-1-carboxylateHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66919946(S)-2-{[5-(3,3-Dimethyl-2-oxo-butoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-pentanedioic acid 5-tert-butyl ester

Product 1

HCID 669201124-((S)-4-tert-Butoxycarbonyl-2-{[5-(3,3-dimethyl-2-oxo-butoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-butyryl)-piperazine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3.5 g (S)-2-{[5-(3,3-dimethyl-2-oxo-butoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-pentanedioic acid 5-tert-butyl ester in 11 ml DMF were added 1.36 ml benzyl 1-piperazinecarboxylate, 3.61 ml N-ethylmorpholine and 2.3 g TOTU. After 2 h the reaction mixture was diluted with ethyl acetate and extracted with aqueous NaHCO3 and aqueous LiCl (4% w/w). The crude product product obtained after evaporation of the solvent (4.4 g) was used in the subsequent reaction.

Workup

  1. extractionextracted with aqueous NaHCO3 and aqueous LiCl (4% w/w)

Sources & evidence

ORD record
ord-4eb0b5eeba2e4b4bb4d595bd9d01951c
Source dataset
uspto-grants-2013_12
Patent number
US08598179B2

Reaction notes

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