Sodium Bicarbonate → HCID 11827521, compound

HRID 857117Notes

Reaction equation

HRID 857117 reaction equation
[CH3:1][C@H:2]1[C:6](=[O:7])[O:5][C@@H:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:3]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].[I:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28]Br.C[Si](C)(C)N[Si](C)(C)C.[Li].C(=O)(O)[O-].[Na+]>C1COCC1>[I:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28][C@:2]1([CH3:1])[C:6](=[O:7])[O:5][C@@H:4]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:3]1[C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 27593613-Iodobenzyl bromideHCID 10638764HCID 10638764, compoundHCID 57426343Lithium bis(trimethylsilyl)amide

Product 1

HCID 11827521HCID 11827521, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
20 °C

Procedure

A solution of benzyl (2S,4S)-4-methyl-5-oxo-2-phenyl-1,3-oxazolidine-3-carboxylate (J. Org. Chem. 2001, 66, 1903) (1.2 g) and 3-iodobenzyl bromide (1.15 g) in THF (8 ml) was added dropwise to a solution of lithium hexamethyldisilazane in THF (1M, 4.1 ml) diluted in THF (32 ml) at −30° C. The mixture was stirred at this temperature and then allowed to warm to 20° C. over 4 h. Aqueous sodium bicarbonate solution was then added and the mixture was extracted with Et2O. The organic phase was separated and dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on a Biotage cartridge (40 g) eluting with EtOAc-petroleum ether (1:9, 1:4) to give the title compound (1.48 g) HPLC RT=9.33 min.

Workup

  1. extractionthe mixture was extracted with Et2O
  2. customThe organic phase was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography on a Biotage cartridge (40 g)
  7. washeluting with EtOAc-petroleum ether (1:9, 1:4)

Sources & evidence

ORD record
ord-098655c8599b4b4da3d7ac20310b7bf3
Source dataset
uspto-grants-2006_12
Patent number
US07144908B2

Reaction notes

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