Imidazole → HCID 86708028, compound

HRID 714126Notes

Reaction equation

HRID 714126 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:12]([N:14]([O:16][CH3:17])[CH3:15])=[O:13])[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[C:23]([Si:27](Cl)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([CH3:26])([CH3:25])[CH3:24]>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:12]([N:14]([O:16][CH3:17])[CH3:15])=[O:13])[CH2:10][O:11][Si:27]([C:23]([CH3:26])([CH3:25])[CH3:24])([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 11032217HCID 11032217, compound

Product 1

HCID 86708028HCID 86708028, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N2-(tert-butoxycarbonyl)-N-methoxy-N-methyl-D-serinamide (1, 1.93 g, 7.78 mmol) and imidazole (1.21 g, 17.81 mmol) in DMF (9 ml) stirred under N2 at room temperature, was treated with neat tert-butyl(chloro)diphenylsilane (2.2 ml, 8.56 mmol) and further stirred for 17 h. Diluted with EtOAc, washed with 5% KHSO4 in water, then sat NaHCO3, dried over Na2SO4, filtered and concentrated. Purified through a chromatographic cartridge of silicagel (50 g) eluted with 10% to 60% EtOAc in hexane to give 3.55 g (94% yield) of title compound as colorless oil. MS: m/z=509.2 (MNa+).

Workup

  1. washwashed with 5% KHSO4 in water
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurified through a chromatographic cartridge of silicagel (50 g)
  6. washeluted with 10% to 60% EtOAc in hexane

Sources & evidence

ORD record
ord-0244dc2c6cc64ccc83c7906bbaed8550
Source dataset
uspto-grants-2015_11
Patent number
US09187415B2

Reaction notes

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