Triethylamine → Propanoic acid, 2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, (2S)-

HRID 1858908Notes

Reaction equation

HRID 1858908 reaction equation
[C:1]([Si:5](Cl)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:26]([OH:31])(=[O:30])[C@H:27]([CH3:29])[OH:28]>C1COCC1.ClCCl>[O:28]([C@@H:27]([CH3:29])[C:26]([OH:31])=[O:30])[Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 94078tert-Butyldiphenylchlorosilane2×HCID 107689L-Lactic Acid

Product 1

HCID 11232725Propanoic acid, 2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, (2S)-Yield 58%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of t-butylchlorodiphenylsilane, TBDPSCl, (7.9 g, 28.9 mmoL) in THF (20 mL) was slowly added via canula into a solution of triethylamine (7.4 mL, 53.1 mmol), DMAP(catalytic amount) and L-(+)-lactic acid 9 (2.0954 g, 26.16 mmol) in THF (20 mL) and dichloromethane (20 mL) at room temperature. The resulting mixture, a white suspension, was stirred at room temperature for 2 days. The reaction mixture was washed sequentially with water, 3N HCl and water, dried over Na2SO4, filtered and solvent was removed under vacuum. The product was purified by column chromatography on silica using EtOAc/hexane=1/3 and 1/1 as eluent to obtain 4.965 g (58%) of 10.

Workup

  1. washThe reaction mixture was washed sequentially with water, 3N HCl and water
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customsolvent was removed under vacuum
  5. customThe product was purified by column chromatography on silica

Sources & evidence

ORD record
ord-57c4d9d5eac64c6bb67c645584a6c57c
Source dataset
uspto-grants-2000_11
Patent number
US06153596

Reaction notes

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