Water → HCID 71610757, compound

HRID 714035Notes

Reaction equation

HRID 714035 reaction equation
O.C([O:9][C:10]1[C:11]([C:42]2[CH:47]=[CH:46][C:45]([F:48])=[CH:44][CH:43]=2)=[CH:12][C:13]([CH2:40][CH3:41])=[C:14]([CH:39]=1)[O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[C:21]([CH2:36][CH2:37][CH3:38])=[C:22]([NH:26][C:27](=[O:35])[CH2:28][C:29]([CH3:34])([CH3:33])[C:30]([OH:32])=[O:31])[CH:23]=[CH:24][CH:25]=1)C1C=CC=CC=1.[H][H]>[Pd].C1COCC1>[CH2:40]([C:13]1[CH:12]=[C:11]([C:42]2[CH:43]=[CH:44][C:45]([F:48])=[CH:46][CH:47]=2)[C:10]([OH:9])=[CH:39][C:14]=1[O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[C:21]([CH2:36][CH2:37][CH3:38])=[C:22]([NH:26][C:27](=[O:35])[CH2:28][C:29]([CH3:34])([CH3:33])[C:30]([OH:32])=[O:31])[CH:23]=[CH:24][CH:25]=1)[CH3:41]

Participants

6

Reactant 3

HCID 962WaterHCID 89690304HCID 89690304, compoundHCID 178418361HCID 178418361, compound3×

Product 1

HCID 71610757HCID 71610757, compoundYield 112.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Hydrogenate a slurry of 10% palladium on charcoal, 50% wet (with water by weight) (13 g) and 4-[[3-[3-[5-benzyloxy-2-ethyl-4-(4-fluorophenyl)phenoxy]propoxy]-2-propyl-phenyl]amino]-2,2-dimethyl-4-oxo-butanoic acid (260 g, 405 mmol)) in THF (1560 mL) starting at a hydrogen pressure of 900 psi. Continue the hydrogenation 20 h while not adding additional hydrogen. Hydrogenate two additional days maintaining hydrogen pressure of 200 psi. Filter the mixture through diatomaceous earth and concentrate the filtrate in vacuo to yield the title compound (251 g, quantitative) as a solid. Excess weight is due to the presence of THF. ES/MS m/z 552 (M+1).

Workup

  1. customthe hydrogenation 20 h
  2. filtrationFilter the mixture through diatomaceous earth
  3. concentrationconcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-d59e3c8d0cd54fe3aae3f409a7aa2759
Source dataset
uspto-grants-2015_11
Patent number
US09187411B2

Reaction notes

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