(4R)-4-phenyl-1,3-oxazolidin-2-one → HCID 53936034, compound

HRID 1033132Notes

Reaction equation

HRID 1033132 reaction equation
[C:1]1([C@@H:7]2[CH2:11][O:10][C:9](=[O:12])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:24][C:25]1[CH:40]=[CH:39][C:28]([C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])=[CH:27][CH:26]=1>C1COCC1>[CH2:32]([O:31][C:29]([C:28]1[CH:27]=[CH:26][C:25]([CH2:24][N:8]2[C@H:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:11][O:10][C:9]2=[O:12])=[CH:40][CH:39]=1)=[O:30])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 730425(4R)-4-phenyl-1,3-oxazolidin-2-oneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 18543917Benzyl 4-(bromomethyl)benzoate

Product 1

HCID 53936034HCID 53936034, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

490 mg (3 mmol) of (4R)-(-)-4-phenyl-2-oxazolidinone are dissolved in 9 ml of absolute THF, first 3.3 ml of sodium bistrimethylsilylamide (1M in THF) and then 1050 mg (3.45 mmol) of benzyl 4-bromomethylbenzoate, dissolved in 2 ml of absolute THF, are added. The crude product is purified by chromatography (eluent: CH2Cl2)

Workup

  1. additionare added
  2. customThe crude product is purified by chromatography (eluent: CH2Cl2)

Sources & evidence

ORD record
ord-a3d61c1e46124cb58c3911e178bf5086
Source dataset
uspto-grants-1994_05
Patent number
US05310499

Reaction notes

Loading…