Ethylmorpholine → 4-[(S)-3-(1-Benzyl-1H-[1,2,3]triazol-4-yl)-2-tert-butoxycarbonylamino-propionyl]-piperazine-1-carboxylic acid butyl ester

HRID 1185572Notes

Reaction equation

HRID 1185572 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([CH2:13][C@H:14]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:15]([OH:17])=O)[N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1CCOCC1)C.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[CH2:56]([O:60][C:61]([N:63]1[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]1)=[O:62])[CH2:57][CH2:58][CH3:59]>CN(C=O)C>[CH2:56]([O:60][C:61]([N:63]1[CH2:68][CH2:67][N:66]([C:15](=[O:17])[C@@H:14]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:13][C:11]2[N:10]=[N:9][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:12]=2)[CH2:65][CH2:64]1)=[O:62])[CH2:57][CH2:58][CH3:59]

Participants

6

Reactant 4

HCID 7525EthylmorpholineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21963126Butyl piperazine-1-carboxylateHCID 68599866(S)-3-(1-Benzyl-1H-[1,2,3]triazol-4-yl)-2-tert-butoxycarbonylamino-propionic acid

Product 1

HCID 685988914-[(S)-3-(1-Benzyl-1H-[1,2,3]triazol-4-yl)-2-tert-butoxycarbonylamino-propionyl]-piperazine-1-carboxylic acid butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 836 mg (S)-3-(1-Benzyl-1H-[1,2,3]triazol-4-yl)-2-tert-butoxycarbonylamino-propionic acid in 20 ml DMF were added 0.61 ml N-ethylmorpholine, 0.79 g TOTU and 449 mg Piperazine-1-carboxylic acid butyl ester. After stirring for 2 h the reaction mixture was concentrated, diluted with ethyl acetate and washed with aqueous LiCl (4%), 0.1 M HCl, saturated aqueous NaHCO3 and brine. The crude product obtained was used without further purification. Yield: 1.14 g.

Workup

  1. concentrationwas concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with aqueous LiCl (4%), 0.1 M HCl, saturated aqueous NaHCO3 and brine

Sources & evidence

ORD record
ord-35ac22e5bf1e4f1788df78efe278f9b8
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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