Triethylamine → HCID 22175197, compound

HRID 1797756Notes

Reaction equation

HRID 1797756 reaction equation
[C:1]([O:5][C:6](=[O:32])[NH:7][CH2:8][C:9]1[N:10]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:11](=[O:27])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:16][C:15]([CH2:25][NH2:26])=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2].Cl[C:34]([O:36][CH2:37][CH3:38])=[O:35].C(N(CC)CC)C>O1CCCC1>[C:1]([O:5][C:6]([NH:7][CH2:8][C:9]1[N:10]([CH2:28][CH:29]([CH3:30])[CH3:31])[C:11](=[O:27])[C:12]2[C:17]([C:18]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[CH:16][C:15]([CH2:25][NH:26][C:34](=[O:35])[O:36][CH2:37][CH3:38])=[CH:14][CH:13]=2)=[O:32])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 22176261HCID 22176261, compound

Product 1

HCID 22175197HCID 22175197, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of crude tert-butyl[6-(aminomethyl)-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.16 g) (Example 285) in tetrahydrofuran (2 mL) were added ethyl chloroformate (0.035 mL, 0.36 mmol) and triethylamine (0.050 mL, 0.36 mmol), and the mixture was stirred at room temperature for 4 h. The reaction mixture was washed with water (4 mL) and concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1 (v/v)) to give ethyl (3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-6-isoquinolinyl)methylcarbamate (0.13 g, 87%) as pale yellow powder.

Workup

  1. washThe reaction mixture was washed with water (4 mL)
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1 (v/v))

Sources & evidence

ORD record
ord-5fdfe23c28c143ee980cbd05a4b715ae
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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