Imidazole → HCID 90406529, compound

HRID 571651Notes

Reaction equation

HRID 571651 reaction equation
[OH:1][CH2:2][C@@H:3]1[S:8][CH2:7][C@@H:6]([CH3:9])[NH:5][C:4]1=[O:10].N1C=CN=C1.[C:16]([Si:20](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:19])([CH3:18])[CH3:17].O>C(Cl)Cl>[Si:20]([O:1][CH2:2][C@@H:3]1[S:8][CH2:7][C@@H:6]([CH3:9])[NH:5][C:4]1=[O:10])([C:16]([CH3:19])([CH3:18])[CH3:17])([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 89519951HCID 89519951, compound

Product 1

HCID 90406529HCID 90406529, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the above crude compound (11, 9.0 g, 0.057 mol) in DCM (150 mL) was added imidazole (7.70 g, 0.113 mol) followed by tert-butyl(chloro)diphenylsilane (17.2 g, 0.0630 mol) under N2 atmosphere. After the addition, the resulting solution was stirred at ambient temperature for 2 hours. Water (100 mL) was added and the mixture was extracted with DCM (3×200 mL). The combined organic fractions were concentrated in vacuo, and the resultant residue was purified by silica gel chromatography (PE: EtOAc=10:1 to 2:1) to give (2S,5R)-2-({[tert-butyl(diphenyl)silyl]oxy}methyl)-5-methylthiomorpholin-3-one (12) that gave a proton NMR spectra consistent with theory.

Workup

  1. additionAfter the addition
  2. extractionthe mixture was extracted with DCM (3×200 mL)
  3. concentrationThe combined organic fractions were concentrated in vacuo
  4. customthe resultant residue was purified by silica gel chromatography (PE: EtOAc=10:1 to 2:1)

Sources & evidence

ORD record
ord-8e15fc1379514e00b6f5939c49fff55a
Source dataset
uspto-grants-2015_05
Patent number
US09029364B2

Reaction notes

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