Diethyl Ether → HCID 54042579, compound

HRID 847313Notes

Reaction equation

HRID 847313 reaction equation
[CH:1]1([CH2:7][C@H:8]2[C@H:12]([CH2:13][C@@H:14]([CH:19]([CH3:21])[CH3:20])[CH:15]([OH:18])CO)[O:11][C:10]([CH3:23])([CH3:22])[N:9]2[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4].CCOCC>C1C=CC=CC=1>[CH:1]1([CH2:7][C@H:8]2[C@H:12]([CH2:13][C@H:14]([CH:15]=[O:18])[CH:19]([CH3:21])[CH3:20])[O:11][C:10]([CH3:22])([CH3:23])[N:9]2[C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 57195921HCID 57195921, compoundHCID 178418268HCID 178418268, compound

Product 1

HCID 54042579HCID 54042579, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

20.0 g (46.8 mmol) of t-butyl (4S,5S)-4-(cyclohexylmethyl)-5-[(2S,3RS)-3,4-dihydroxy-2-isopropylbutyl]-2,2-dimethyl-3-oxazolidinecarboxylate are dissolved in 250 ml of benzene, cooled to 5° and treated portionwise within 10 minutes with 20.8 g (47 mmol) of lead tetraacetate. After stirring at 5° for 4 hours 500 ml of ether are added and the reaction mixture is stirred for a further 15 minutes. Thereafter, the reaction mixture is filtered and the filtrate is evaporated under reduced pressure. Chromatography of the residue on 300 g of silica gel with methylene chloride as the eluting agent yields 15.9 g of t-butyl (4S,5S)-4-(cyclohexylmethyl)-5-[(S)-2-formyl-3-methylbutyl]-2,2-dimethyl-3-oxazolidinecarboxylate as an oil, MS: 380 (M-CH3)+.

Workup

  1. temperaturecooled to 5°
  2. additionare added
  3. filtrationThereafter, the reaction mixture is filtered
  4. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-63d2ab3961454edbbce8fb26fe7f799b
Source dataset
uspto-grants-1992_08
Patent number
US05140011

Reaction notes

Loading…