Ethyl Acetate → HCID 178458454, compound

HRID 2275484Notes

Reaction equation

HRID 2275484 reaction equation
C([O:8][C:9](=[O:62])[C@:10]([CH3:61])([CH2:53][O:54][CH:55]1[CH2:60][CH2:59][CH2:58][CH2:57][O:56]1)[CH2:11][C@H:12]([NH:26][C:27]([C:29]1[N:30]=[N:31][N:32](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:33]=1)=[O:28])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)C1C=CC=CC=1.CCOC(C)=O>[Pd]>[C:17]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:18]=[CH:19][C:14]([CH2:13][C@@H:12]([NH:26][C:27]([C:29]2[N:30]=[N:31][NH:32][CH:33]=2)=[O:28])[CH2:11][C@@:10]([CH3:61])([CH2:53][O:54][CH:55]2[CH2:60][CH2:59][CH2:58][CH2:57][O:56]2)[C:9]([OH:62])=[O:8])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 89964490HCID 89964490, compound

Product 1

HCID 178458454HCID 178458454, compoundYield 156.2%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(2S,4R)-5-Biphenyl-4-yl-2-methyl-2-(tetrahydropyran-2-yloxymethyl)-4-[(1-trityl-1H-1,2,3-triazole-4-carbonyl)amino]pentanoic acid benzyl ester (7.5 g, 9.1 mmol) was combined with EtOAc (80 mL, 800 mmol). The resulting clear solution was purged with nitrogen and 10% Pd/C (0.05:0.45, Palladium:carbon black, 1.0 g, 0.94 mmol) was added. The resulting mixture was purged with hydrogen and then hydrogenated overnight at room temperature. The mixture was purged with nitrogen, the solids were filtered off, and the solvent was removed by rotary evaporation to yield the title compound (7 g).

Workup

  1. additionwas added
  2. customThe resulting mixture was purged with hydrogen
  3. customhydrogenated overnight
  4. customat room temperature
  5. customThe mixture was purged with nitrogen
  6. filtrationthe solids were filtered off
  7. customthe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-3994e33bd9534a8caacc3812d0404076
Source dataset
uspto-grants-2015_09
Patent number
US09126956B2

Reaction notes

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