Triethylamine → 3-(1-ethoxycarbonyl-3-phenylpropyl)amino-3-methyl-1,2-dihydro-2-oxo-3H-indole

HRID 845332Notes

Reaction equation

HRID 845332 reaction equation
Br[C:2]1([CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:11].[NH2:13][CH:14]([CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16].C(N(CC)CC)C>CCOCC>[CH2:18]([O:17][C:15]([CH:14]([NH:13][C:2]1([CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:11])[CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4646380Ethyl 2-amino-4-phenylbutanoateHCID 217664783-Bromo-3-methyloxindole

Product 1

HCID 201323733-(1-ethoxycarbonyl-3-phenylpropyl)amino-3-methyl-1,2-dihydro-2-oxo-3H-indole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2.5 g 3-bromo-3-methyloxindole, 2 g ethyl 2-amino-4-phenylbutyrate and 1.6 ml triethylamine in 150 ml ether was refluxed for 48 hours. The resulting crude product was partitioned between 50% potassium carbonate solution and ethyl acetate. The organic phase was dried (MgSO4) and concentrated. Chromatography at the residue (silica, ether) afforded 3-(1-ethoxycarbonyl-3-phenylpropyl)amino-3-methyl-1,2-dihydro-2-oxo-3H-indole as a mixture of diastereomers.

Workup

  1. customThe resulting crude product was partitioned between 50% potassium carbonate solution and ethyl acetate
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1bca0e84aaf3409dbd466fb4829356f6
Source dataset
uspto-grants-1988_07
Patent number
US04757068

Reaction notes

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