Water → HCID 86611581, compound

HRID 1432096Notes

Reaction equation

HRID 1432096 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH:18]1[CH2:22][CH2:21][C:20](=[O:23])[O:19]1)[CH2:10][C@H:11]([CH3:17])[CH2:12][CH2:13]C(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.O>C1C=CC=CC=1.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([CH:18]1[CH2:22][CH2:21][C:20](=[O:23])[O:19]1)[CH2:10][CH:11]([CH3:17])[CH:12]=[CH2:13])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 962WaterHCID 1049PyridineHCID 68541748HCID 68541748, compound

Product 1

HCID 86611581HCID 86611581, compound

Reagents, catalysts & solvents 2

HCID 165397Cupric acetate monohydrateCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 2.19 g (6.67 mmol) (R)-6-tert-butoxycarbonylamino-4-methyl-6-(5-oxo-tetra-hydro-furan-2-yl)-hexanoic acid, 0.293 g (1.46 mmol) copper(II)acetate monohydrate, 0.2 ml pyridine and 5.4 g (12.0 mmol) Pb(OAc)4 in 45 ml benzene is refluxed under nitrogen for 18 h. The mixture is cooled to rt, water is added and the organic phase is washed with water and 5% aqueous NaHCO3. The organic phase is dried with Na2SO4, filtered and evaporated. The residue is purified by chromatography on silica gel (EtOAc/hexane 1:6 and 1:4) to yield the title compound.

Workup

  1. temperatureis refluxed under nitrogen for 18 h
  2. washthe organic phase is washed with water and 5% aqueous NaHCO3
  3. dry with materialThe organic phase is dried with Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by chromatography on silica gel (EtOAc/hexane 1:6 and 1:4)

Sources & evidence

ORD record
ord-86637b11662c403babbb1f911c7e44d5
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

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