Water → HCID 70170307, compound

HRID 617615Notes

Reaction equation

HRID 617615 reaction equation
[H-].[Na+].[C:3]([O:6][CH2:7][C:8]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])([CH2:18][CH3:19])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)(=[O:5])[CH3:4].[C:28]1([CH2:34][CH2:35][CH2:36][CH2:37]I)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>CN(C)C=O>[C:3]([O:6][CH2:7][C:8]([NH:20][C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])([CH2:18][CH3:19])[CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:37][CH2:36][CH2:35][CH2:34][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:15][CH:16]=1)(=[O:5])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 12709818(4-Iodobutyl)benzeneHCID 53825896HCID 53825896, compound

Product 1

HCID 70170307HCID 70170307, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (0.65 g) in dimethylformamide (16 ml) was added a solution of 2-tert-butoxycarbonylamino-2-ethyl-4-(4-hydroxyphenyl)butyl acetate (6.0 g) in dimethylformamide (50 ml) at 0° C. and the mixture was stirred at room temperature for an hour. 4-Phenyl-butyl iodide (90 g) was added to the solution at 0° C. and the mixture was allowed to stand at room temperature overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and a saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure and the residue obtained was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=1:1) to give the subject compound (3.6 g). 1H-NMR (270 MHz, CDCl3) δ: 0.89 (3H, t, J=7.3 Hz), 1.45 (9H, s), 1.65-2.01 (8H, m), 2.08 (3H, s), 2.50 (2H, t, J=8.6 Hz), 2.67 (2H, t, J=6.6 Hz), 3.94 (2H, t, J=5.94 Hz), 4.22 (2H, dd, J=16, 11 Hz), 4.42 (1H, br. s), 6.80 (2H, d, J=8.6 Hz) 7.07 (2H, d, J=8.6 Hz), 7.16 (3H, t, J=7.3 Hz), 7.26-7.31 (2H, m)

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materiala saturated brine and dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled away under reduced pressure
  5. customthe residue obtained
  6. customwas purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-f8d90c24ddc84d87920cb36cf2567b4e
Source dataset
uspto-grants-1999_09
Patent number
US05948820

Reaction notes

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