Hydrochloric Acid → HCID 57160385, compound

HRID 1975478Notes

Reaction equation

HRID 1975478 reaction equation
[CH2:1]([O:4][C:5]([N:7]([CH2:9][C@H:10]([CH2:21][NH:22][C:23]([O:25][CH2:26][CH:27]=[CH2:28])=[O:24])[C@H:11]([O:13][Si](C(C)(C)C)(C)C)[CH3:12])[CH3:8])=[O:6])[CH:2]=[CH2:3].Cl>C(OCC)(=O)C>[CH2:1]([O:4][C:5]([N:7]([CH2:9][C@@H:10]([C@H:11]([OH:13])[CH3:12])[CH2:21][NH:22][C:23]([O:25][CH2:26][CH:27]=[CH2:28])=[O:24])[CH3:8])=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54413927HCID 54413927, compound

Product 1

HCID 57160385HCID 57160385, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (2S,3R)-1-(N-allyloxycarbonyl-N-methylamino)-2-allyloxycarbonylaminomethyl-3-t-butyldimethylsilyloxybutane (28.18 g) in ethyl acetate (500 ml) was added hydrochloric acid (6N, 17 ml), and the resulting mixture was stirred at ambient temperature for 2 hours. The reaction mixture was washed in turn with cold water, aqueous sodium hydrogen carbonate, and brine, and dried over magnesium sulfate. Evaporation of the solvent gave a residue which was chromatographed on silica gel (500 ml) eluting with a mixture of n-hexane and ethyl acetate (9:1-6:4, V/V) to give (2S,3R)-2-(N-allyloxycarbonyl-N-methylaminomethyl)-1-allyloxycarbonylamino-3-hydroxybutane (20.11 g).

Workup

  1. washThe reaction mixture was washed in turn with cold water, aqueous sodium hydrogen carbonate, and brine
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation of the solvent
  4. customgave a residue which
  5. customwas chromatographed on silica gel (500 ml)
  6. washeluting with a mixture of n-hexane and ethyl acetate (9:1-6:4, V/V)

Sources & evidence

ORD record
ord-eb5c4871e4314568a41c3d84aec24051
Source dataset
uspto-grants-1994_02
Patent number
US05286721

Reaction notes

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