Benzyl Bromide → 4-[N-benzyl-N-(2-methoxycarbonyl-1-methylethyl)aminoacetyl]-7-benzyloxyindole-2-carboxylic acid ethyl ester

HRID 1762948Notes

Reaction equation

HRID 1762948 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:33])[CH2:17][N:18]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH:19]([CH3:25])[CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:12]=[CH:11][C:10]=2[OH:34])=[O:6])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[CH2:41](Br)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=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:33])[CH2:17][N:18]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH:19]([CH3:25])[CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:12]=[CH:11][C:10]=2[O:34][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:6])[CH3:3]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 131056554-[N-benzyl-N-(2-methoxycarbonyl-1-methylethyl)aminoacetyl]-7-hydroxyindole-2-carboxylic acid ethyl ester hydrochloride

Product 1

HCID 132434364-[N-benzyl-N-(2-methoxycarbonyl-1-methylethyl)aminoacetyl]-7-benzyloxyindole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

48.8 g of 4-[N-benzyl-N-(2-methoxycarbonyl-1-methylethyl)aminoacetyl]-7-hydroxyindole-2-carboxylic acid ethyl ester hydrochloride, 41.4 g of potassium carbonate, and 25 ml of benzyl bromide are heated under reflux for 6 hours in 900 ml of acetone. After cooling, the reaction mixture is concentrated to dryness, the residue is taken up in ethyl acetate and saturated sodium bicarbonate solution, the organic phase is separated and extracted three times with saturated sodium bicarbonate solution. The organic phase is washed with water, dried, concentrated, and the residue is recrystallized from ethyl acetate/n-hexane, thus obtaining 42.5 g of 4-[N-benzyl-N-(2-methoxycarbonyl-1-methylethyl)aminoacetyl]-7-benzyloxyindole-2-carboxylic acid ethyl ester, mp 120°-123° C.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture is concentrated to dryness
  3. customsaturated sodium bicarbonate solution, the organic phase is separated
  4. extractionextracted three times with saturated sodium bicarbonate solution
  5. washThe organic phase is washed with water
  6. customdried
  7. concentrationconcentrated
  8. customthe residue is recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-82e5739f48e1454388b525423cc7c279
Source dataset
uspto-grants-1989_05
Patent number
US04835175

Reaction notes

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