Hydrochloric Acid → HCID 86607344, compound

HRID 1455573Notes

Reaction equation

HRID 1455573 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C@@H:4]([NH:13]C(OCC1C=CC=CC=1)=O)[CH2:5][C:6]([F:12])([F:11])[CH2:7][CH:8]([CH3:10])[CH3:9].[ClH:25].O1CCOCC1>CO.[Pd]>[ClH:25].[CH3:1][O:2][C:3](=[O:24])[C@@H:4]([NH2:13])[CH2:5][C:6]([F:12])([F:11])[CH2:7][CH:8]([CH3:9])[CH3:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 57535354HCID 57535354, compound

Product 1

HCID 86607344HCID 86607344, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

A solution of (S)-2-benzyloxycarbonylamino-4,4-difluoro-6-methyl-heptanoic acid methyl ester: (333 mg, 0.97 mmol) in methanol (10 mL) and 4 M HCl in dioxane (4 mmol, 1 mL) is hydrogenated over 10% Pd/C (150 mg) at 55 psi. After 7 hr, another portion of 10% Pd/C (200 mg) is added and the hydrogenation resumed. After 5.5 hr, the reaction did not progress. Catalyst is filtered and the filtrate is concentrated in vacuum and subjected to the hydrogenation conditions. After 6.5 hr, the catalyst is removed by filtration over a pad of Celite, and the filtrate is concentrated in vacuum to afford (S)-2-amino-4,4-difluoro-6-methyl-heptanoic acid methyl ester hydrochloride as a sticky solid (240 mg, quant.).

Workup

  1. waitAfter 5.5 hr
  2. filtrationCatalyst is filtered
  3. concentrationthe filtrate is concentrated in vacuum
  4. waitAfter 6.5 hr
  5. customthe catalyst is removed by filtration over a pad of Celite
  6. concentrationthe filtrate is concentrated in vacuum

Sources & evidence

ORD record
ord-596d4aaef4e842caa7ab74a1f0fc2138
Source dataset
uspto-grants-2009_01
Patent number
US07482448B2

Reaction notes

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