Diisopropylethylamine → HCID 178496329, compound

HRID 448608Notes

Reaction equation

HRID 448608 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[N:3]=[N:2]1.CCN([CH:15]([CH3:17])C)C(C)C.CN([C:21]([O:25]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:42]1([C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)[CH:47]=[CH:46][C:45]([CH2:48][C@@H:49]([NH:58]C(OC(C)(C)C)=O)[CH2:50][C@:51]([CH2:56][OH:57])([CH3:55])[C:52]([OH:54])=[O:53])=[CH:44][CH:43]=1>CN(C=O)C.Cl.O1CCOCC1.CCO>[CH3:21][O:25][CH2:15][CH2:17][O:54][C:52](=[O:53])[C@@:51]([CH2:56][OH:57])([CH3:55])[CH2:50][C@H:49]([NH:58][C:6]([C:4]1[NH:3][N:2]=[N:1][CH:5]=1)=[O:8])[CH2:48][C:45]1[CH:46]=[CH:47][C:42]([C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)=[CH:43][CH:44]=1

Participants

9

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 68181022(2S,4R)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxymethyl-2-methyl-pentanoic acid

Product 1

HCID 178496329HCID 178496329, compound

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

1,2,3-Triazole-4-carboxylic acid (49.7 mg, 439 μmol, 0.8 eq.), DIPEA (230 mL), and HATU (167 mg, 439 μmol, 0.8 eq.) were dissolved in DMF (0.5 mL) and stirred at room temperature for 5 minutes to yield the activated acid. (2S,4R)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxymethyl-2-methyl-pentanoic acid (218 mg, 527 μmol, 1.0 eq.) was dissolved in 4 M of HCl in dioxane (2 mL) and EtOH (4 mL). The mixture was stirred overnight at 70° C. The product was evaporated under vacuum and azeotroped with toluene, then combined with the activated acid. After 15 minutes, the reaction was quenched with AcOH and the product was purified by preparative HPLC and lyophilized to yield the title compound (40 mg). MS m/z [M+H]+ calc'd for C25H30N4O5, 467.22. found 467.4.

Workup

  1. customto yield the activated acid
  2. stirringThe mixture was stirred overnight at 70° C
  3. customThe product was evaporated under vacuum
  4. customazeotroped with toluene
  5. waitAfter 15 minutes
  6. customthe reaction was quenched with AcOH
  7. customthe product was purified by preparative HPLC

Sources & evidence

ORD record
ord-0a4fed51586b442b81c01aa5cc2a0066
Source dataset
uspto-grants-2013_07
Patent number
US08481044B2

Reaction notes

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