Potassium Carbonate → Methyl 4-[({2-[2-(4-bromobenzyloxy)phenyl]ethyl}-tert-butoxycarbonylamino)methyl]benzoate

HRID 1672610Notes

Reaction equation

HRID 1672610 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:18][C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1)[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[OH:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34]Br)=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][O:17][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][CH2:9][N:8]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:27][CH:28]=2)[C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromideHCID 22014997Methyl 4-{[(tert-butoxycarbonyl)-(2-hydroxyphenethyl)-amino]methyl}benzoate

Product 1

HCID 57864402Methyl 4-[({2-[2-(4-bromobenzyloxy)phenyl]ethyl}-tert-butoxycarbonylamino)methyl]benzoateYield 96.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5 g (12.87 mmol) of methyl 4-({tert-butoxycarbonyl-[2-(2-hydroxyphenyl)ethyl]amino}methyl)benzoate from Example 3A in 100 ml of dry acetonitrile is mixed with 3.89 g (15.57 mmol) of 4-bromobenzyl bromide and 2.69 g (19.46 mmol) of anhydrous potassium carbonate and heated to reflux for 12 hours. The mixture is then concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution and dried over sodium sulfate. The resulting organic phase is concentrated. The crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 20:1→10:1). 6.88 g (12.4 mmol, 89% yield) of a solid are obtained.

Workup

  1. temperatureheated
  2. temperatureto reflux for 12 hours
  3. concentrationThe mixture is then concentrated to dryness
  4. washwashed with water and saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationThe resulting organic phase is concentrated
  7. customThe crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 20:1→10:1)

Sources & evidence

ORD record
ord-c82cb369c43348cb87ae236a0be0c168
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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