p-Anisoyl chloride → HCID 57043850, compound

HRID 393459Notes

Reaction equation

HRID 393459 reaction equation
[CH3:1][O:2][C:3](=[O:34])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([C:26]2[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=2[Cl:33])=[O:25])=[CH:19][CH:18]=1)[NH:5][C:6]([C:8]1([CH2:13][CH2:14][NH2:15])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].[CH3:35][O:36][C:37]1[CH:45]=[CH:44][C:40]([C:41](Cl)=[O:42])=[CH:39][CH:38]=1.CCN(C(C)C)C(C)C>ClCCl>[CH3:1][O:2][C:3](=[O:34])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([C:26]2[C:27]([Cl:33])=[CH:28][CH:29]=[CH:30][C:31]=2[Cl:32])=[O:25])=[CH:19][CH:18]=1)[NH:5][C:6]([C:8]1([CH2:13][CH2:14][NH:15][C:41]([C:40]2[CH:44]=[CH:45][C:37]([O:36][CH3:35])=[CH:38][CH:39]=2)=[O:42])[CH2:9][CH2:10][CH2:11][CH2:12]1)=[O:7]

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 81531DiisopropylethylamineHCID 54376481HCID 54376481, compound

Product 1

HCID 57043850HCID 57043850, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[1-(2-aminoethyl)cyclopentyl]-carbonyl]-L-phenylalanine methyl ester (0.2 mmol, 101 mg) and 4-methoxybenzoyl chloride (0.25 mmol, 52.1 mg) in dichloromethane (1 mL) was added DIPEA (0.3 mmol, 38.7 mg) at room temperature. The reaction mixture was stirred for 15 h at room temperature and then diluted with 20 mL of dichloromethane. The dichloromethane layer was washed successively with water (20 mL) and brine solution (20 mL) and was dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration of the solvent afforded a crude product which was purified by revesrsed phase HPLC to obtain 0.1 g (78%) of a yellow syrup. HR MS (C33H35Cl2N3O6): Obs. mass, 662.1778. Calcd. mass, 662.1801 (M+Na).

Workup

  1. washThe dichloromethane layer was washed successively with water (20 mL) and brine solution (20 mL)
  2. dry with materialwas dried over anhydrous magnesium sulfate
  3. filtrationFiltration of the drying agent and concentration of the solvent
  4. customafforded a crude product which
  5. customwas purified by revesrsed phase HPLC

Sources & evidence

ORD record
ord-b1bf8bc0712f4e21bb51666e08b5ae83
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

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