(N-Acetyl)-(4R)-benzyl-2-oxazolidinone → 4-Benzyl-3-[3-(4-benzyloxy-3-cyclopentyloxyphenyl)-4-nitrobutyryl]-oxazolidin-2-one

HRID 1819337Notes

Reaction equation

HRID 1819337 reaction equation
[C:1]([N:4]1[CH:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:7][O:6][C:5]1=[O:16])(=[O:3])[CH3:2].C(NC(C)C)(C)C.[Li].[CH2:25]([O:32][C:33]1[CH:38]=[CH:37][C:36]([CH:39]=[CH:40][N+:41]([O-:43])=[O:42])=[CH:35][C:34]=1[O:44][CH:45]1[CH2:49][CH2:48][CH2:47][CH2:46]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1>[CH2:9]([CH:8]1[CH2:7][O:6][C:5](=[O:16])[N:4]1[C:1](=[O:3])[CH2:2][CH:39]([C:36]1[CH:37]=[CH:38][C:33]([O:32][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[C:34]([O:44][CH:45]2[CH2:49][CH2:48][CH2:47][CH2:46]2)[CH:35]=1)[CH2:40][N+:41]([O-:43])=[O:42])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 4605613(N-Acetyl)-(4R)-benzyl-2-oxazolidinoneHCID 45051747Lithium diisopropylamineHCID 688282011-Benzyloxy-2-cyclopentyloxy-4-(2-nitrovinyl)benzene

Product 1

HCID 688284324-Benzyl-3-[3-(4-benzyloxy-3-cyclopentyloxyphenyl)-4-nitrobutyryl]-oxazolidin-2-oneYield 76.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A mixture of 3-acetyl-4-benzyl-oxazolidin-2-one (2.1 g, 9.4 mmol) in THF (40 mL) was stirred under N2 at −78° C. Lithium diisopropyl amine (5.2 mL, 10.3 mmol, 2.0 M in heptane/THF/ethylbenzene) was then added dropwise. The mixture was stirred for 20 min. 1-Benzyloxy-2-cyclopentyloxy-4-(2-nitrovinyl)benzene (3.2 g, 9.4 mmol) dissolved in 20 mL THF was cannulated over and the mixture was stirred for 2 h at −78° C. After quenching the reaction sat. NH4Cl, the mixture was warmed to r.t., extracted with CH3Cl, washed with water and brine, dried and concentrated. Filtration of the solids with 1:1 hexane/EtOAc, afforded 4 g of white solids. Yield: 75%.

Workup

  1. stirringThe mixture was stirred for 20 min
  2. stirringwas stirred for 2 h at −78° C
  3. customAfter quenching the reaction sat. NH4Cl
  4. temperaturethe mixture was warmed to r.t.
  5. extractionextracted with CH3Cl
  6. washwashed with water and brine
  7. customdried
  8. concentrationconcentrated
  9. filtrationFiltration of the solids with 1:1 hexane/EtOAc

Sources & evidence

ORD record
ord-e67b446939074fd5853e007a1ce0e0d6
Source dataset
uspto-grants-2009_10
Patent number
US07601742B2

Reaction notes

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