Imidazole → HCID 59370731, compound

HRID 1873978Notes

Reaction equation

HRID 1873978 reaction equation
[CH2:1]([N:8]([CH2:21][CH2:22][O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:9][C@@H:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1)[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.Cl[Si:37]([CH2:42][CH3:43])([CH2:40][CH3:41])[CH2:38][CH3:39].O>CN(C=O)C>[CH2:1]([N:8]([CH2:21][CH2:22][O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:9][C@@H:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1)[O:11][Si:37]([CH2:42][CH3:43])([CH2:40][CH3:41])[CH2:38][CH3:39])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 13819ChlorotriethylsilaneHCID 59370738HCID 59370738, compound

Product 1

HCID 59370731HCID 59370731, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(R)-2-(Benzyl(2-(benzyloxy)ethyl)amino)-1-(3-nitrophenyl)ethanol (30.371 g) which can be prepared according to the method described in Reference example 57, etc. and imidazole (6.1318 g; manufactured by Tokyo Chemical Industry, Co., Ltd.) were dissolved in dehydrated DMF (150 mL), added with chlorotriethylsilane (15.1 mL; manufactured by Shin-Etsu Chemical Co., Ltd.), followed by stirring overnight at room temperature. The reaction solution was poured to water and extracted twice with ethyl acetate. The organic layer was washed twice with water and once with brine and dried over magnesium sulfate. After concentrating under reduced pressure, the residue was purified by column chromatography (“COLUMN-A”; n-hexane:ethyl acetate=100:0→87:13) to obtain the title compound (36.655 g).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe organic layer was washed twice with water and once with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationAfter concentrating under reduced pressure
  5. customthe residue was purified by column chromatography (“COLUMN-A”; n-hexane:ethyl acetate=100:0→87:13)

Sources & evidence

ORD record
ord-bfd9e5dac0434cf1a9497db90984818c
Source dataset
uspto-grants-2012_11
Patent number
US08304443B2

Reaction notes

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