Triethylamine → HCID 18765894, compound

HRID 481013Notes

Reaction equation

HRID 481013 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[NH:12][C:11]([CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:32][O:33][CH2:34][CH2:35][NH:36][CH2:37][CH3:38])=[C:10]1[C:39]([O:41][CH3:42])=[O:40].[C:43](=O)([O:49]C(C)(C)C)[O:44][C:45]([CH3:48])([CH3:47])[CH3:46].C(N(CC)CC)C>ClCCl>[CH3:42][O:41][C:39]([C:10]1[CH:9]([C:3]2[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[NH:12][C:11]=1[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:32][O:33][CH2:34][CH2:35][N:36]([C:43]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:49])[CH2:37][CH3:38])=[O:40]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 18765886HCID 18765886, compound

Product 1

HCID 18765894HCID 18765894, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled stirred solution of dimethyl 4-(2,6-dichlorophenyl)-2-[2-(2-{[2-(ethylamino)ethoxy]methyl}phenyl)ethyl]-6-(2-methoxy-2-oxoethyl)-1,4-dihydro-3,5-pyridinedicarboxylate (700 mg/1.13 mmol) in dichloromethane (50 ml) was added di-t-butyl carbonate (297 mg/1.36 mmol) and triethylamine (172 mg/1.70 mmol). The reaction mixture was warmed to room temperature and stirred for 1.5 h. The reaction mixture was quenched with water. The separated organic layer was washed with water, dried over MgSO4, filtered and concentrated to give a crude mixture. This crude was purified by column chromatography on silica gel (CH2Cl2:MeOH=40:1) to afford a yellow amorphous (813 mg/quant.).

Workup

  1. customThe reaction mixture was quenched with water
  2. washThe separated organic layer was washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f5e0b6fed9a0479b9c6495e070f487cd
Source dataset
uspto-grants-2003_11
Patent number
US06653313B2

Reaction notes

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