Imidazole → HCID 58464132, compound

HRID 1917547Notes

Reaction equation

HRID 1917547 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH:5]([OH:22])[CH2:6][N:7]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:2].[C:24]([Si:28](Cl)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([CH3:27])([CH3:26])[CH3:25].N1C=CN=C1>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH2:1]([O:3][C:4](=[O:23])[CH:5]([O:22][Si:28]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:6][N:7]([CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH3:2]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 67436072HCID 67436072, compound

Product 1

HCID 58464132HCID 58464132, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

(5.8 g, 18.6 mmol) (RS)-3-Dibenzylamino-2-hydroxy-propionic acid ethyl ester (CAS 93715-75-4) was dissolved in DMF (40 ml) and tert-butylchlorodiphenylsilane (6.76 ml, 26 mmol, 1.4 equiv.), Imidazole (1.9 g, 27.9 mmol, 1.5 equiv.) and DMAP (227 mg, 1.9 mmol, 0.1 equiv.) were added at room temperature. The mixture was stirred for 3 hours at 80° C. The reaction mixture was evaporated and extracted with saturated NaHCO3 solution and two times with EtOAc. The organic layers were extracted with brine, dried over Na2SO4 and evaporated to dryness. The crude product was purified by flash chromatography on silica gel column and eluting with an ethyl acetate:heptane gradient 0:100 to 40:60. The desired (RS)-2-(tert-butyl-diphenyl-silanyloxy)-3-dibenzylamino-propionic acid ethyl ester (8.1 g, 79% yield) was obtained as a colorless oil, MS: m/e=552.5 (M+H+).

Workup

  1. customThe reaction mixture was evaporated
  2. extractionextracted with saturated NaHCO3 solution and two times with EtOAc
  3. extractionThe organic layers were extracted with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customThe crude product was purified by flash chromatography on silica gel column
  7. washeluting with an ethyl acetate

Sources & evidence

ORD record
ord-45a09b282afa467fbba6fdbeadde1c5d
Source dataset
uspto-grants-2013_12
Patent number
US08618296B2

Reaction notes

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