Triethylamine → (4S,5S)-4-((tert-Butyldiphenylsilyloxy)methyl)-5-phenyloxazolidin-2-one

HRID 929944Notes

Reaction equation

HRID 929944 reaction equation
[OH:1][CH2:2][C@H:3]1[C@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:6][C:5](=[O:14])[NH:4]1.CCN(CC)CC.[CH3:22][C:23]([Si:26](Cl)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([CH3:25])[CH3:24]>CN(C1C=CN=CC=1)C.CN(C=O)C>[Si:26]([O:1][CH2:2][C@H:3]1[C@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:6][C:5](=[O:14])[NH:4]1)([C:23]([CH3:25])([CH3:24])[CH3:22])([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 94078tert-ButyldiphenylchlorosilaneHCID 11116891(4S,5S)-4-Hydroxymethyl-5-phenyl-oxazolidin-2-one

Product 1

HCID 86718526(4S,5S)-4-((tert-Butyldiphenylsilyloxy)methyl)-5-phenyloxazolidin-2-oneYield 57.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of (4S,5S)-4-hydroxymethyl-5-phenyl-oxazolidin-2-one (3.50 g, 17.2 mmol), NEt3 (4.80 mL, 34.4 mmol), and DMAP (105 mg, 861 μmol) in DMF (20 mL) was added dropwise TBDPSCl (4.86 mL, 18.9 mmol) at room temperature. The reaction was stirred for 3 hours at room temperature. The reaction mixture was then concentrated and diluted with TBME, the organic layers were separated, washed with aqueous NaHCO3 and brine, dried over MgSO4, and concentrated. The residue was purified by column chromatography (120 g SiO2) using EtOAc in heptane from 0% to 60% in order to give the title compound as a white solid (4.28 g, 57%). LC-MS: [M+H] 432.2; Rt 1.36 min; (LCMS method 2).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. additiondiluted with TBME
  3. customthe organic layers were separated
  4. washwashed with aqueous NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (120 g SiO2)

Sources & evidence

ORD record
ord-4f470b8dd2a4424da64fa65619ff1c39
Source dataset
uspto-grants-2016_03
Patent number
US09296733B2

Reaction notes

Loading…