Sodium Hydroxide → HCID 57947864, compound

HRID 416405Notes

Reaction equation

HRID 416405 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][C@H:8]([N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH3:19])[CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])(=O)C.[OH-].[Na+]>C1COCC1.CO.CCOC(C)=O>[Si:11]([O:10][CH2:9][C@@H:8]([N:18]([CH3:19])[C:20](=[O:21])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:7][CH2:6][CH2:5][OH:4])([C:14]([CH3:16])([CH3:15])[CH3:17])([CH3:12])[CH3:13]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 57947560HCID 57947560, compound

Product 1

HCID 57947864HCID 57947864, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-4-(tert-butoxycarbonyl(methyl)amino)-5-(tert-butyldimethylsilyloxy)pentyl acetate (0.124 mol) in THF (200 mL) and MeOH (50 mL) was added sodium hydroxide (2 N, 93 mL, 0.186 mol) at RT The reaction was stirred at RT for 2 h and LC-MS indicated the reaction was completed. The reaction mixture was diluted with EtOAc and the organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated. The resulting residue was purified on silica gel column using a mixture of hexanes and EtOAc to give (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-5-hydroxypentan-2-yl(methyl)carbamate (37.9 g, 88%). LRMS (M+H+-Boc) m/z 248.2.

Workup

  1. washthe organic layer was washed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue was purified on silica gel column
  6. additiona mixture of hexanes and EtOAc

Sources & evidence

ORD record
ord-851716a94ecd437fb20ae595c0183bbb
Source dataset
uspto-grants-2012_01
Patent number
US08088793B2

Reaction notes

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