Hydrochloric Acid → HCID 54208445, compound

HRID 2271008Notes

Reaction equation

HRID 2271008 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C@H:11]([N:13]([CH2:18][CH2:19]OS(C)(=O)=O)[S:14]([CH3:17])(=[O:16])=[O:15])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl>CN(C=O)C>[CH2:1]([O:8][CH2:9][C@H:10]1[C@@H:11]([CH3:12])[N:13]([S:14]([CH3:17])(=[O:16])=[O:15])[CH2:18][CH2:19][N:25]1[C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 57099433HCID 57099433, compound

Product 1

HCID 54208445HCID 54208445, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of (2R,3R)-O-benzyl-2-tert-butoxycarbonylamino-3-[N-(2-methanesulfonyloxyethyl)-N-methanesulfonylamino]butanol (2.6 g) in dry DMF (15 ml) was added dropwise to a suspension of sodium hydride (60% dispersion in mineral oil, 189 mg) in dry DMF (10 ml) at 4° C. over 20 minutes. The mixture was stirred at same temperature for 45 minutes and then poured into a mixture of ice and 1N HCl (8 ml). The mixture was extracted with AcOEt. The organic layer was washed with saturated aqueous NaCl solution, dried over MgSO4 and concentrated in vacuo. The residue was purified by SiO2 column chromatography (eluent: AcOEt in n-hexane 40% and 50%) to give 2.1 g of (2R,3R)-2-benzyloxymethyl-1-tert-butoxycarbonyl-4-methanesulfonyl-3-methylpiperazine as an oil.

Workup

  1. extractionThe mixture was extracted with AcOEt
  2. washThe organic layer was washed with saturated aqueous NaCl solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by SiO2 column chromatography (eluent: AcOEt in n-hexane 40% and 50%)

Sources & evidence

ORD record
ord-78b5e86c512e4a21b90fc5277bcb29da
Source dataset
uspto-grants-2001_12
Patent number
US06333324B1

Reaction notes

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