Diisopropylethylamine → HCID 178452368, compound

HRID 1185575Notes

Reaction equation

HRID 1185575 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[C:15]([OH:20])=[N:16][O:17][C:18]=1[CH3:19])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:54]([O:58][C:59]([N:61]1[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]1)=[O:60])[CH2:55][CH2:56][CH3:57]>CN(C=O)C>[CH2:54]([O:58][C:59]([N:61]1[CH2:66][CH2:65][N:64]([C:10](=[O:12])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][C:14]2[C:15]([OH:20])=[N:16][O:17][C:18]=2[CH3:19])[CH2:63][CH2:62]1)=[O:60])[CH2:55][CH2:56][CH3:57]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21963126Butyl piperazine-1-carboxylateHCID 178435009HCID 178435009, compound

Product 1

HCID 178452368HCID 178452368, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 110 mg (S)-2-tert-Butoxycarbonylamino-3-(3-hydroxy-5-methyl-isoxazol-4-yl)-propionic acid in 2 ml DMF were added 0.07 ml DIPEA, 107 mg HATU and 50 mg Piperazine-1-carboxylic acid butyl ester. After stirring for 2 h the reaction mixture was concentrated, diluted with DCM and washed with aqueous LiCl (4%). The crude product obtained was used without further purification. Yield: 146 mg.

Workup

  1. concentrationwas concentrated
  2. additiondiluted with DCM
  3. washwashed with aqueous LiCl (4%)

Sources & evidence

ORD record
ord-8b40e1297b5b43bba98b5504c0063030
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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