Hydrochloric Acid → 1-allyloxycarbonylamino-2-(N-allyloxycarbonylaminomethyl)butan-3-ol

HRID 1975461Notes

Reaction equation

HRID 1975461 reaction equation
[CH2:1]([O:4][C:5]([NH:7][CH2:8][CH:9]([CH2:20][NH:21][C:22]([O:24][CH2:25][CH:26]=[CH2:27])=[O:23])[CH:10]([O:12][Si](C(C)(C)C)(C)C)[CH3:11])=[O:6])[CH:2]=[CH2:3].Cl>C(#N)C>[CH2:25]([O:24][C:22]([NH:21][CH2:20][CH:9]([CH2:8][NH:7][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[CH:10]([OH:12])[CH3:11])=[O:23])[CH:26]=[CH2:27]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19099269HCID 19099269, compound

Product 1

HCID 190993021-allyloxycarbonylamino-2-(N-allyloxycarbonylaminomethyl)butan-3-olYield 101.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3.98 g of 1-allyloxycarbonylamino-2-(N-allyloxycarbonylaminomethyl)-3-t-butyldimethylsilyloxybutane in 20 ml of acetonitrile was added 2 ml of concentrated hydrochloric acid at 0° C. After stirring for 3 hours at room temperature, the mixture was extracted with chloroform and the organic layer was washed with saturated sodium hydrogen carbonate and brine, and dried over anhydrous magnesium sulfate. Evaporation of the solvent followed by a column chromatography on silica gel (hexane:ethyl acetate=1:1) gave 2.88 g of 1-allyloxycarbonylamino-2-(N-allyloxycarbonylaminomethyl)butan-3-ol quantitatively.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washthe organic layer was washed with saturated sodium hydrogen carbonate and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-0a05ea8233cb4da290ffc78be6b25810
Source dataset
uspto-grants-1994_02
Patent number
US05286721

Reaction notes

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