Diisopropylethylamine → HCID 178459161, compound

HRID 448634Notes

Reaction equation

HRID 448634 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[N:3]=[N:2]1.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.[CH2:42]([O:49][C:50]([CH2:52][O:53][C:54](=[O:75])[C@@:55]([CH2:73][OH:74])([CH3:72])[CH2:56][C@H:57]([NH2:71])[CH2:58][C:59]1[CH:64]=[CH:63][C:62]([C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)=[CH:61][CH:60]=1)=[O:51])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CN(C=O)C>[CH2:42]([O:49][C:50]([CH2:52][O:53][C:54](=[O:75])[C@@:55]([CH2:73][OH:74])([CH3:72])[CH2:56][C@H:57]([NH:71][C:6]([C:4]1[NH:3][N:2]=[N:1][CH:5]=1)=[O:8])[CH2:58][C:59]1[CH:60]=[CH:61][C:62]([C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)=[CH:63][CH:64]=1)=[O:51])[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1401204-Carboxy-1,2,3-triazoleHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68181047HCID 68181047, compound

Product 1

HCID 178459161HCID 178459161, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,2,3-Triazole-4-carboxylic acid (14 mg, 124 μmol), DIPEA (86.3 μL, 496 μmol) and HATU (47.1 mg, 124 μmol) were combined in DMF (0.2 mL) and stirred for 5 minutes at room temperature. This was then combined with (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid benzyloxycarbonylmethyl ester (57.2 mg, 124 μmol). The resulting mixture was stirred for 15 minutes and the reaction was quenched with AcOH. The product purified by preparative HPLC and lyophilized to yield the title compound (19 mg; purity 95%). MS m/z [M+H]+ calc'd for C31H32N4O6, 557.23. found 557.2.

Workup

  1. stirringThe resulting mixture was stirred for 15 minutes
  2. customthe reaction was quenched with AcOH
  3. customThe product purified by preparative HPLC

Sources & evidence

ORD record
ord-134ffba2f2e04a3196bebb2df058586b
Source dataset
uspto-grants-2013_07
Patent number
US08481044B2

Reaction notes

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