Sodium hydride → HCID 57302609, compound

HRID 2296658Notes

Reaction equation

HRID 2296658 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+].[NH4+].[Cl-]>C1COCC1>[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 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86585806HCID 86585806, compound

Product 1

HCID 57302609HCID 57302609, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (2R,3S)-O-benzyl-2-tert-butoxycarbonylamino-3-[N-(2-methanesulfonyloxyethyl)-N-methanesulfonylamino]butanol (1.1 g) in dry THF (15 ml) was added dropwise to a suspension of sodium hydride (60% dispersion in mineral oil, 80.1 mg) in dry THF (8 ml) at 4° C. over 15 minutes. The mixture was stirred at the same temperature for 3.5 hours and then poured into saturated aqueous NH4Cl solution. 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 0.80 g of (2R,3S)-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-691f4cdd37e84e72a8edee3395f7c7b8
Source dataset
uspto-grants-2002_12
Patent number
US06489324B2

Reaction notes

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