Toluene → HCID 4867618, compound

HRID 987921Notes

Reaction equation

HRID 987921 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]([CH2:20][CH:21]=[CH:22][C:23]([N:25]2[CH:29]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:28][O:27][C:26]2=[O:37])=[O:24])[O:10][C:9]1([CH3:39])[CH3:38])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Si](C)(C)[O:42][C:43]([CH:45]=[CH2:46])=[CH2:44].[Cl-].C([Al+]CC)C.C1(C)C=CC=CC=1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]([CH2:20][CH:21]2[CH2:44][C:43](=[O:42])[CH2:45][CH2:46][CH:22]2[C:23]([N:25]2[CH:29]([CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:28][O:27][C:26]2=[O:37])=[O:24])[O:10][C:9]1([CH3:39])[CH3:38])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 1140TolueneHCID 5546572-(Trimethylsiloxy)-1,3-butadieneHCID 16686102Diethyl aluminum chlorideHCID 69853422HCID 69853422, compound

Product 1

HCID 4867618HCID 4867618, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 4-Benzyl-5-[4-(-4-benzyl-2-oxo-oxazolidin-3-yl)-4-oxo-but-2-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (13.35 g, 25 mmol) in dichloromethane (500 ml) was stirred at −78° C. under nitrogen during the addition of 2-trimethylsiloxy-1,3-butadiene (26 ml, 150 mmol) and 1.8 M diethylaluminium chloride solution in toluene (70 ml, 125 mmol). The resulting pale yellow solution was stirred at −78° C. for 48 hours then slowly added to vigorously stirred, ice-cold 1 M hydrogen chloride aqueous solution. After 1 hour the two layers were separated and the aqueous phase was extracted twice with ethyl acetate. The combined organic layers were washed with a saturated aqueous sodium hydrogen carbonate solution and brine, dried (anhydrous magnesium sulfate) and concentrated in vacuo to give, after purification by flash chromatography on silica gel (ethyl acetate/hexane 1/9 to 4/6), 4-Benzyl-5-[2-(4-benzyl-2-oxo-oxazolidine-3-carbonyl)-5-oxo-cyclohexylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (8.7 g) as a white foam.

Workup

  1. additionthen slowly added
  2. stirringto vigorously stirred
  3. customAfter 1 hour the two layers were separated
  4. extractionthe aqueous phase was extracted twice with ethyl acetate
  5. washThe combined organic layers were washed with a saturated aqueous sodium hydrogen carbonate solution and brine
  6. dry with materialdried (anhydrous magnesium sulfate)
  7. concentrationconcentrated in vacuo
  8. customto give
  9. customafter purification by flash chromatography on silica gel (ethyl acetate/hexane 1/9 to 4/6), 4-Benzyl-5-[2-(4-benzyl-2-oxo-oxazolidine-3-carbonyl)-5-oxo-cyclohexylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (8.7 g) as a white foam

Sources & evidence

ORD record
ord-6931f03efb16401d8a0378fcd87cf13e
Source dataset
uspto-grants-2003_10
Patent number
US06632826B1

Reaction notes

Loading…