Hydrochloric Acid → HCID 86727233, compound

HRID 336332Notes

Reaction equation

HRID 336332 reaction equation
[OH:1][CH2:2][C@H:3]1[O:7][C:6](=[O:8])[NH:5][CH2:4]1.N1C=CN=C1.[C:14]([Si:18](Cl)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:17])([CH3:16])[CH3:15].Cl>CN(C)C=O>[Si:18]([O:1][CH2:2][C@H:3]1[O:7][C:6](=[O:8])[NH:5][CH2:4]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 2793787(5S)-5-(hydroxymethyl)-1,3-oxazolidin-2-one

Product 1

HCID 86727233HCID 86727233, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-5-(hydroxymethyl)oxazolidin-2-one (570 mg, 4.87 mmol, as described by Danielmeier, K.; Steckhan, E. Tet. Asymmetry, 6(5), 1995, 1181) and imidazole (331 mg, 4.87 mmol) were dissolved in dimethylformamide (5 mL) and cooled to 0° C. tert-Butylchlorodiphenylsilane (1.34 g, 4.87 mmol) was added dropwise at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 5 hours. The mixture was was poured into 0.5 N HCl (50 ml), and the resultant mixture was extracted with ethyl acetate. The layers were separated, and the organic phase was washed with saturated sodium bicarbonate, water and brine. The organic phase was dried over sodium sufate and the solvent removed to afford crude material that was purified on a silica gel column (50% ethyl acetate in hexanes) to give the title compound (1.28 g, 74.0%). 1H NMR (300 MHz, DMSO-d6) δ: 1.0 (s, 9H) 3.3-3.6 (m, 2H) 3.6-3.9 (m, 2H) 4.6-4.8 (m, 1H) 7.3-7.8 (m, 11H). MS (ES) (M+23)+: 278 for the Na+ adduct of C20H25NO3Si.

Workup

  1. additionwas added dropwise at 0° C
  2. extractionthe resultant mixture was extracted with ethyl acetate
  3. customThe layers were separated
  4. washthe organic phase was washed with saturated sodium bicarbonate, water and brine
  5. dry with materialThe organic phase was dried over sodium sufate
  6. customthe solvent removed
  7. customto afford crude material that
  8. customwas purified on a silica gel column (50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7bb80479bf2b49279bcb76a6f745569b
Source dataset
uspto-grants-2014_11
Patent number
US08889671B2

Reaction notes

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