Triethylamine → HCID 53889396, compound

HRID 1588855Notes

Reaction equation

C(N(CC)CC)C.[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17](Cl)=[O:18].[NH2:20][CH2:21][C:22]([N:24]([CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:23].C(=O)([O-])O.[Na+]>ClCCCl.ClCCl>[C:35]([O:34][C:32]([CH2:31][N:24]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:22]([CH2:21][NH:20][C:17]([C:9]1[NH:8][C:16]2[C:11]([CH:10]=1)=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:18])=[O:23])=[O:33])([CH3:38])([CH3:36])[CH3:37]

Participants

Conditions

Temperature: 25 °C

Procedure

Triethylamine (0.7 g), and then 2-indolecarbonyl chloride (1.2 g) dissolved in 1,2-dichloroethane (35 cc), are added to a solution, stirred at a temperature in the region of 25° C., of tert-butyl 2-(2-amino-N-phenylacetamido)acetate (1.2 g) in 1,2-dichloroethane (35 cc). The reaction mixture is stirred for 18 hours at a temperature in the region of 25° C. Dichloromethane (250 cc) is then added, followed by saturated aqueous sodium hydrogen carbonate solution (125 cc). The organic phase is washed with distilled water (2×125 cc), dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization in acetonitrile, N-[N-(tert-butoxycarbonylmethyl) phenylcarbamoylmethyl]-2-indolecarboxamide (1 g), m.p. 203° C., is obtained.

Workup

additionare added to a solution
washThe organic phase is washed with distilled water (2×125 cc)
dry with materialdried over magnesium sulphate
concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
customAfter recrystallization in acetonitrile

Sources & evidence

ORD record: ord-f244c3fc1be84910a1347e01649f3308
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05223529

Reaction notes

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