Dimethylformamide → 4-[(S)-2-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoyl]-piperazine-1-carboxylic acid butyl ester

HRID 1970490Notes

Reaction equation

HRID 1970490 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH2:15][O:16][Si:17]([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)C(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1CCOCC1)C.[CH2:42]([O:46]N1CCNCC1=C=O)[CH2:43][CH2:44][CH3:45].[B-](F)(F)(F)F.CCOC(C(C#N)=N[O:67][C:68]([N:72]([CH3:74])[CH3:73])=[N+](C)C)=O.[CH3:77][N:78]([CH:80]=[O:81])[CH3:79]>C(OCC)(=O)C>[CH2:42]([O:46][C:80]([N:78]1[CH2:79][CH2:73][N:72]([C:68](=[O:67])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH2:13][CH2:14][CH2:15][O:16][Si:17]([C:30]([CH3:31])([CH3:33])[CH3:32])([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:74][CH2:77]1)=[O:81])[CH2:43][CH2:44][CH3:45]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 7525EthylmorpholineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66856371(S)-2-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoic acidHCID 866504721-Butoxy-carbonylpiperazine

Product 1

HCID 668543564-[(S)-2-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoyl]-piperazine-1-carboxylic acid butyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.6 g (S)-2-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid in 8 ml DMF were added 1.7 ml N-ethylmorpholine, 1.0 g 1-butoxy-carbonylpiperazine hydrotrifluoroacetate and 1.1 g TOTU. The solution was stirred for 12 h before being diluted with ethyl acetate and extracted subsequently with aqueous LiCl (4%), 0.1 M HCl and saturated aqueous NaHCO3. The crude product obtained after evaporation of the solvent was used without further purification. Yield: 1.8 g.

Workup

  1. extractionextracted subsequently with aqueous LiCl (4%), 0.1 M HCl and saturated aqueous NaHCO3

Sources & evidence

ORD record
ord-00fa13226e384e0288545a43d46153a9
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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