Benzyl Alcohol → Benzyl 3-(1-tert-butoxycarbonyl-2-n-butylimidazol-4-yl)-2-(3,4-methylenedioxyphenyl)propionate

HRID 1533275Notes

Reaction equation

HRID 1533275 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:14]([O:18][C:19]([N:21]1[CH:25]=[C:24]([CH2:26][CH:27]([C:39]2[CH:44]=[CH:43][C:42]3[O:45][CH2:46][O:47][C:41]=3[CH:40]=2)[C:28](N2[C@@H](C(C)C)COC2=O)=[O:29])[N:23]=[C:22]1[CH2:48][CH2:49][CH2:50][CH3:51])=[O:20])([CH3:17])([CH3:16])[CH3:15]>O1CCCC1>[C:14]([O:18][C:19]([N:21]1[CH:25]=[C:24]([CH2:26][CH:27]([C:39]2[CH:44]=[CH:43][C:42]3[O:45][CH2:46][O:47][C:41]=3[CH:40]=2)[C:28]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:29])[N:23]=[C:22]1[CH2:48][CH2:49][CH2:50][CH3:51])=[O:20])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 56994932(4S)-3-[3-(1-tert-butoxycarbonyl-2-n-butylimidazol-4-yl)-2-(3,4-methylenedioxyphenyl)propionyl]-4-isopropyloxazolidin-2-oneHCID 178418339Butyllithium

Product 1

HCID 22012330Benzyl 3-(1-tert-butoxycarbonyl-2-n-butylimidazol-4-yl)-2-(3,4-methylenedioxyphenyl)propionateYield 78.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl alcohol (1.29 g) in tetrahydrofuran (60 ml) was added dropwise n-butyl lithium (6.6 ml, 1.6M n-hexane solution) at 2-8° C. and the mixture was stirred for 20 minutes. A solution of (4S)-3-[3-(1-tert-butoxycarbonyl-2-n-butylimidazol-4-yl)-2-(3,4-methylenedioxyphenyl)propionyl]-4-isopropyloxazolidin-2-one (4.86 g) was added dropwise to the mixture and the resulting solution was stirred at 2° C. for 2 hours. The reaction was quenched with saturated ammonium chloride aqueous solution, and then the solution was extracted with ethyl acetate. The organic layer was washed successively with saturated sodium bicarbonate aqueous solution and brine. Drying, filtering and removal of the solvents afforded a crude product. The crude product was purified by a silica gel column chromatography (eluent; n-hexane:ethyl acetate=4:1) to give benzyl 3-(1-tert-butoxycarbonyl-2-n-butylimidazol-4-yl)-2-(3,4-methylenedioxyphenyl)propionate (2R:2S=1:4) (3.67 g) as a slightly yellow oil.

Workup

  1. stirringthe resulting solution was stirred at 2° C. for 2 hours
  2. customThe reaction was quenched with saturated ammonium chloride aqueous solution
  3. extractionthe solution was extracted with ethyl acetate
  4. washThe organic layer was washed successively with saturated sodium bicarbonate aqueous solution and brine
  5. customDrying
  6. filtrationfiltering
  7. customremoval of the solvents
  8. customafforded a crude product
  9. customThe crude product was purified by a silica gel column chromatography (eluent; n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-a79a41b725ca41f0ae9e9cca164c8d93
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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