HCID 15219011, compound → (2S,4S,5S)-5-benzyloxycarbonylamino-6-cyclohexyl-2-isopropyl-4-hexanolide

HRID 1743070Notes

Reaction equation

HRID 1743070 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C@@H:20]([OH:28])[CH2:21][C@@H:22]([CH:25]([CH3:27])[CH3:26])[CH2:23][OH:24])[CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)[C@H:20]1[O:28][C:23](=[O:24])[C@H:22]([CH:25]([CH3:26])[CH3:27])[CH2:21]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 15219011HCID 15219011, compoundHCID 131709961Jones' reagent

Product 1

HCID 18637741(2S,4S,5S)-5-benzyloxycarbonylamino-6-cyclohexyl-2-isopropyl-4-hexanolideYield 57%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of diol prepared in Example 19 (500 mg, 1.3 mmol) and Jones Reagent 2.7M (1.9 mL, 5.2 mmol) in 10 mL acetone was stirred vigorously at 10° C. for 3 hours. The reaction mixture was filtered through a plug of Celite® and the plug was washed repeatedly with diethyl ether. The ether layer was washed 2×5 mL with saturated brine, dried over MgSO4 and concentrated in vacuo to give a white solid. The solid was flash chromatographed on silica eluting with 20% EtOAc/80% hexanes to give 286 mg (57%) of the title compound which was identical to the lactone prepared in Example 24.

Workup

  1. filtrationThe reaction mixture was filtered through a plug of Celite®
  2. washthe plug was washed repeatedly with diethyl ether
  3. washThe ether layer was washed 2×5 mL with saturated brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give a white solid
  7. customchromatographed on silica eluting with 20% EtOAc/80% hexanes

Sources & evidence

ORD record
ord-d25b1f1d089641f29886b6296b20b511
Source dataset
uspto-grants-1994_08
Patent number
US05342981

Reaction notes

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