Diethyl Ether → (2S)-2-t-Butoxycarbonylamino-3-n-hexanoyloxy-2-methyl-1-propanal

HRID 604543

Reaction equation

HRID 604543 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[C:12]([O:16][C:17]([NH:19][C@@:20]([CH3:32])([CH2:23][O:24][C:25](=[O:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:21][OH:22])=[O:18])([CH3:15])([CH3:14])[CH3:13].CCOCC>C(Cl)Cl>[C:12]([O:16][C:17]([NH:19][C@@:20]([CH3:32])([CH2:23][O:24][C:25](=[O:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:21]=[O:22])=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11630856(2R)-2-t-Butoxycarbonylamino-3-n-hexanoyloxy-2-methyl-1-propanolHCID 178418287HCID 178418287, compound

Product 1

HCID 20721242(2S)-2-t-Butoxycarbonylamino-3-n-hexanoyloxy-2-methyl-1-propanalYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Molecular sieve 4A (220 g) and pyridinium chlorochromate (43.6 g, 0.202 mol) were added to a solution of (2R)-2-t-butoxycarbonylamino-3-n-hexanoyloxy-2-methyl-1-propanol (30.7 g, 0.101 mol) obtained in Reference example 1 (1a) in methylene chloride (600 mL) under ice-cooling and the mixture was stirred at room temperature for 2 hours. Ether was added to the reaction mixture, the mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate, 10:1-5:1) to obtain the title compound (28.8 g, yield: 95%).

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-ef9800e3a3694b34a9aa7b891b4d8a93
Source dataset
uspto-grants-2011_03
Patent number
US07910617B2

Linked notes

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