4-Carboxy-1,2,3-triazole → HCID 178473661, compound

HRID 535195Notes

Reaction equation

HRID 535195 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[N:3]=[N:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:33]([O:35][C:36]([O:38][CH2:39][O:40][C:41](=[O:62])[C@@:42]([CH2:60][OH:61])([CH3:59])[CH2:43][C@H:44]([NH2:58])[CH2:45][C:46]1[CH:51]=[CH:50][C:49]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[CH:48][CH:47]=1)=[O:37])[CH3:34]>CN(C=O)C.CCN(C(C)C)C(C)C>[CH2:33]([O:35][C:36]([O:38][CH2:39][O:40][C:41](=[O:62])[C@@:42]([CH2:60][OH:61])([CH3:59])[CH2:43][C@H:44]([NH:58][C:6]([C:4]1[NH:3][N:2]=[N:1][CH:5]=1)=[O:8])[CH2:45][C:46]1[CH:47]=[CH:48][C:49]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[CH:50][CH:51]=1)=[O:37])[CH3:34]

Participants

6

Reactant 3

HCID 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 68181053(2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid ethoxycarbonyloxymethyl ester

Product 1

HCID 178473661HCID 178473661, compoundYield 8,161.3%

Reagents, catalysts & solvents 2

HCID 81531DiisopropylethylamineCatalystHCID 6228DimethylformamideSolvent

Procedure

1,2,3-Triazole-4-carboxylic acid (14 mg, 124 nmol), DIPEA (86.3 mL, 496 nmol) and HATU (47.1 mg, 124 nmol) 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 ethoxycarbonyloxymethyl ester (51 mg, 120 nmol). 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 (5 mg; purity 90%). MS m/z [M+H]+ calc'd for C26H30N4O2, 511.21. found 511.6.

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-9e41ecabf94f4d708af3476f731d79a6
Source dataset
uspto-grants-2014_10
Patent number
US08853427B2

Reaction notes

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