HCID 67372163, compound → HCID 67374187, compound

HRID 1677059Notes

Reaction equation

HRID 1677059 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[C@H:5]([NH:17]C(OC(C)(C)C)=O)[CH2:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)=O)[CH3:2]>Cl.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C@H:5]1[CH2:6][CH2:7][C@@H:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[NH:17]1)=[O:25])[CH3:2]

Participants

3

Reactant 1

HCID 67372163HCID 67372163, compound

Product 1

HCID 67374187HCID 67374187, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

A 4 N hydrochloric acid/ethyl acetate solution (90 mL) was added to (R)-2-t-butoxycarbonylamino-5-(4-fluorophenyl)-5-oxovaleric acid ethyl ester (6.33 g), and the resultant was stirred at room temperature for 2 hours. The solvent was removed under a vacuum, and ethanol (50 mL) and 10% palladium on carbon (6 g, 50% water content) was added, and under a hydrogen atmosphere, stirring was continued for 20 hours at room temperature. The catalyst was filtered off on celite, and the solvent was removed under vacuum. The resultant was diluted in ethyl acetate and washed with sodium bicarbonate aqueous solution and brine, in sequence. The solvent was removed under vacuum, and the resultant was purified with silica gel column chromatography (heptane/ethyl acetate), and the title compound (3.11 g) was obtained. The physical property values are as follows.

Workup

  1. customThe solvent was removed under a vacuum, and ethanol (50 mL) and 10% palladium on carbon (6 g, 50% water content)
  2. additionwas added
  3. stirringunder a hydrogen atmosphere, stirring
  4. waitwas continued for 20 hours at room temperature
  5. filtrationThe catalyst was filtered off on celite
  6. customthe solvent was removed under vacuum
  7. additionThe resultant was diluted in ethyl acetate
  8. washwashed with sodium bicarbonate aqueous solution and brine, in sequence
  9. customThe solvent was removed under vacuum
  10. customthe resultant was purified with silica gel column chromatography (heptane/ethyl acetate)

Sources & evidence

ORD record
ord-aafc4c7ddc9344dfb4f22978f417a762
Source dataset
uspto-grants-2011_08
Patent number
US08008293B2

Reaction notes

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