Acetic Acid → HCID 59496653, compound

HRID 449498Notes

Reaction equation

HRID 449498 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9](=[CH:14][C:15]1[CH:16]=[N:17][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=2[F:28])=[CH:19][CH:20]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>[Pd].CO>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:14][C:15]1[CH:16]=[N:17][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=2[F:28])=[CH:19][CH:20]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 441036D-PsicoseHCID 67541207HCID 67541207, compound

Product 1

HCID 59496653HCID 59496653, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon (10 mg) was added to a mixture of methyl 2-[(tert-butoxycarbonyl)amino]-3-[6-(2,3-difluorophenyl)pyridin-3-yl]acrylate (70 mg, 0.2 mmol) in methanol (3 mL) and acetic acid (0.5 mL, 9 mmol). The reaction was shaken in parr shaker under H2 at 60 Psi for 5 h. The reaction was complete by LC-MS, this was filtered and concentrated under reduced pressure to give crude methyl 2-(tert-butoxycarbonylamino)-3-(6-(2,3-difluorophenyl)pyridin-3-yl)propanoate (0.07 g, 100%) as an oil. Analytical LCMS (M+H)+: m/z=393.0.

Workup

  1. filtrationthis was filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-04cc720764f047b0b9a7b2f0701b9859
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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