Diethyl Ether → (2S)-2-t-Butoxycarbonylamino-2-ethyl-3-n-hexanoyloxy-1-propanol

HRID 604553Notes

Reaction equation

HRID 604553 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[C:22]([O:26][C:27]([NH:29][C@@:30]([CH2:42][CH3:43])([CH2:33][O:34][C:35](=[O:41])[CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:31][OH:32])=[O:28])([CH3:25])([CH3:24])[CH3:23].CCOCC>C(Cl)Cl>[C:22]([O:26][C:27]([NH:29][C@:30]([CH2:42][CH3:43])([CH2:33][O:34][C:35](=[O:41])[CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:31][OH:32])=[O:28])([CH3:24])([CH3:25])[CH3:23]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2724130Cornforth reagentHCID 86596707(2R)-2-t-Butoxycarbonylamino-2-ethyl-3-n-hexanoyloxy-1-propanol

Product 1

HCID 86614364(2S)-2-t-Butoxycarbonylamino-2-ethyl-3-n-hexanoyloxy-1-propanolYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Molecular sieve 4A (117 g) and pyridinium dichromate (117 g, 311 mmol) were added to a solution of (2R)-2-t-butoxycarbonylamino-2-ethyl-3-n-hexanoyloxy-1-propanol (66.7 g, 210 mmol) obtained in Reference example 2 (2a) in methylene chloride (700 mL) under ice-cooling and the mixture was stirred at room temperature for 2 hours. Ether was added to the reaction mixture and the mixture was filtered. The filtrate was evaporated under reduced pressure and the residue was purified by silica gel chromatography (hexane:ethyl acetate, 10:1-5:1) to obtain the title compound (45.9 g, yield: 69%).

Workup

  1. temperaturecooling
  2. filtrationthe mixture was filtered
  3. customThe filtrate was evaporated under reduced pressure
  4. customthe residue was purified by silica gel chromatography (hexane:ethyl acetate, 10:1-5:1)

Sources & evidence

ORD record
ord-afcb526928d5407baef446fb87afb15f
Source dataset
uspto-grants-2011_03
Patent number
US07910617B2

Reaction notes

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