Ammonium Chloride → methyl (S)-4-(benzyloxymethoxy)-2-(tert-butyldimethylsiloxy)butanoate

HRID 1775769Notes

Reaction equation

HRID 1775769 reaction equation
[O:1]([C@@H:9]([CH2:14][CH2:15][OH:16])[C:10]([O:12][CH3:13])=[O:11])[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].C(N(C(C)C)CC)(C)C.Cl[CH2:27][O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[Cl-].[NH4+]>ClCCl>[CH2:29]([O:28][CH2:27][O:16][CH2:15][CH2:14][C@H:9]([O:1][Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3])[C:10]([O:12][CH3:13])=[O:11])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 137983Benzyl chloromethyl etherHCID 11107713(S)-methyl 2-(tert-butyldimethylsilyloxy)-4-hydroxybutanoate

Product 1

HCID 131734747methyl (S)-4-(benzyloxymethoxy)-2-(tert-butyldimethylsiloxy)butanoateYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(Step 2) To methyl (S)-2-(tert-butyldimethylsiloxy)-4-hydroxybutanoate (220 mg, 0.886 mmol) obtained in Step 1, dichloromethane (0.89 mL), diisopropylethylamine (0.464 mL, 2.66 mmol), and {(chloromethoxy)methyl}benzene (0.30 mL, 2.21 mmol) were added, and the resulting mixture was stirred at room temperature for 1.5 hours. To the reaction mixture, a saturated aqueous ammonium chloride solution was added, and the resulting mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=20/80), whereby methyl (S)-4-(benzyloxymethoxy)-2-(tert-butyldimethylsiloxy)butanoate (191 mg, 59%) was obtained,

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=20/80)

Sources & evidence

ORD record
ord-25cab32b60034ccdb95f9f324cf76dae
Source dataset
uspto-grants-2016_02
Patent number
US09260459B2

Reaction notes

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