Hydrochloric Acid → HCID 19099237, compound

HRID 1975481Notes

Reaction equation

HRID 1975481 reaction equation
[CH2:1]([O:4][C:5]([N:7]([CH2:9][CH:10]([CH2:21][N:22]([C:24]([O:26][CH2:27][CH:28]=[CH2:29])=[O:25])[CH3:23])[CH:11]([O:13][Si](C(C)(C)C)(C)C)[CH3:12])[CH3:8])=[O:6])[CH:2]=[CH2:3].Cl.[OH2:31]>C(OCC)(=O)C>[CH2:27]([O:26][C:24]([N:22]([CH2:21][CH:10]([CH2:9][N:7]([C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[CH3:8])[C:11]([OH:13])([OH:31])[CH3:12])[CH3:23])=[O:25])[CH:28]=[CH2:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 19099311HCID 19099311, compound

Product 1

HCID 19099237HCID 19099237, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-(N-allyloxycarbonyl-N-methylamino)-2-(N-allyloxycarbonyl-N-methylaminomethyl)-3-(t-butyldimethylsilyloxy)butane (123 g) in ethyl acetate (1.2 l) was added 6N-aqueous hydrochloric acid (240 ml) at ambient temperature. After stirring at the same temperature for 2.5 hours, to the mixture was added water (1 l) and the organic layer was separated. The organic layer was washed successively with 1N-aqueous sodium hydroxide (1 l), saturated aqueous ammonium chloride (500 ml), and brine (500 ml). After the solution was dried over magnesium sulfate, removal of the solvents gave a residue. The residue was chromatographed on silica gel (1 l) eluting with a mixture of n-hexane and ethyl acetate (95:5-40:60, V/V) to give 1-(N-allyloxycarbonyl-N-methylamino)-2-(N-allyloxycarbonyl-N-methylaminomethyl)-3-hydroxybutan-3-ol (83.18 g).

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed successively with 1N-aqueous sodium hydroxide (1 l), saturated aqueous ammonium chloride (500 ml), and brine (500 ml)
  3. dry with materialAfter the solution was dried over magnesium sulfate, removal of the solvents
  4. customgave a residue
  5. customThe residue was chromatographed on silica gel (1 l)
  6. washeluting with a mixture of n-hexane and ethyl acetate (95:5-40:60, V/V)

Sources & evidence

ORD record
ord-a2a45610ea0e45c880d9c5cc651e3481
Source dataset
uspto-grants-1994_02
Patent number
US05286721

Reaction notes

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