Benzyl Bromide → HCID 13243446, compound

HRID 1762954Notes

Reaction equation

HRID 1762954 reaction equation
Cl.[CH2:2]([O:4][C:5]([C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[C:13]([C:16](=[O:23])[CH2:17][NH:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:12]=[CH:11][C:10]=2[OH:24])=[O:6])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CC(C)=O>[CH2:2]([O:4][C:5]([C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[C:13]([C:16](=[O:23])[CH2:17][N:18]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:19]([CH3:20])([CH3:22])[CH3:21])[CH:12]=[CH:11][C:10]=2[O:24][CH2:16][C:13]1[CH:14]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:6])[CH3:3]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 13093613HCID 13093613, compound

Product 1

HCID 13243446HCID 13243446, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

53.6 g of 4-(N-tert-butylaminoacetyl)-7-hydroxyindole-2-carboxylic acid ethyl ester hydrochloride is combined with 59.3 g of potassium carbonate, 63.6 ml of benzyl bromide, and 1000 ml of acetone and heated under reflux for 6 hours. The mixture is then concentrated under vacuum and the residue combined with ethyl acetate and saturated sodium bicarbonate solution. The organic phase is washed three times with sodium bicarbonate solution and once with water, dried over calcium sulfate, and concentrated. The residue is recrystallized twice from ethyl acetate/hexane, thus obtaining 47 g of 7-benzyloxy-4-(N-benzyl-N-tert-butylaminoacetyl)indole-2-carboxylic acid ethyl ester, mp 155°-157° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 6 hours
  3. concentrationThe mixture is then concentrated under vacuum
  4. washThe organic phase is washed three times with sodium bicarbonate solution
  5. dry with materialonce with water, dried over calcium sulfate
  6. concentrationconcentrated
  7. customThe residue is recrystallized twice from ethyl acetate/hexane

Sources & evidence

ORD record
ord-b9a5fad4eec64832b9777d68b5e8d57c
Source dataset
uspto-grants-1989_05
Patent number
US04835175

Reaction notes

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