Water → HCID 178424151, compound

HRID 2275492Notes

Reaction equation

HRID 2275492 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:18][C:19]([C:21]2[N:22]=[N:23][NH:24][CH:25]=2)=[O:20])[CH2:10][C@:11]([CH2:16][OH:17])([CH3:15])[C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1.[CH3:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[OH:17][CH2:16][C@:11]([CH3:15])([CH2:10][C@H:9]([NH:18][C:19]([C:21]1[N:22]=[N:23][NH:24][CH:25]=1)=[O:20])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[CH3:26])=[CH:3][CH:4]=1)[C:12]([OH:14])=[O:13]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 178459152HCID 178459152, compound

Product 1

HCID 178424151HCID 178424151, compoundYield 34.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

(2S,4R)-5-(4-bromophenyl)-2-hydroxymethyl-2-methyl-4-[(1H-[1,2,3]triazole-4-carbonyl)amino]pentanoic acid (38 mg, 92 μmol) was combined with 2-methylphenylboronic acid (25.1 mg, 185 μmol), sodium carbonate (29.4 mg, 277 μmol), water (0.2 mL) and dioxane (1.5 mL). The reaction vessel was sealed, air was removed by vacuum, and the vessel was purged with nitrogen. Tetrakis(triphenylphosphine)palladium(0) (21.4 mg, 18 μmol) was quickly added and air was removed by vacuum. The mixture was heated at 90° C. for 45 minutes. The mixture was acidified to pH ˜3 and filtered, and the solvate was concentrated. The residue was dissolved in AcOH (0.7 mL) and purified by preparative HPLC to yield the title compound (13.3 mg). MS m/z [M+H]+ calc'd for C23H26N4O4, 423.20. found 423.2.

Workup

  1. customThe reaction vessel was sealed
  2. customair was removed by vacuum
  3. customthe vessel was purged with nitrogen
  4. customair was removed by vacuum
  5. filtrationfiltered
  6. concentrationthe solvate was concentrated
  7. dissolutionThe residue was dissolved in AcOH (0.7 mL)
  8. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-76728a9519714f2eadd94a1d34570388
Source dataset
uspto-grants-2015_09
Patent number
US09126956B2

Reaction notes

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