Pyridine → HCID 20610281, compound

HRID 433664Notes

Reaction equation

HRID 433664 reaction equation
ClCCl.[CH2:4]([O:6][C:7](=[O:37])[CH:8]([NH:30][C:31]([O:33][CH2:34][CH:35]=[CH2:36])=[O:32])[CH2:9][C:10]1[O:14][N:13]=[C:12]([CH:15]2[CH2:19][CH2:18][CH2:17][N:16]2[C:20](=[O:29])[CH2:21][C:22]2[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=2)[CH:11]=1)[CH3:5].[Cl:38][C:39]1[CH:47]=[CH:46][CH:45]=[C:44]([Cl:48])[C:40]=1[C:41](Cl)=[O:42].N1C=CC=CC=1>C(OCC)(=O)C>[CH2:4]([O:6][C:7](=[O:37])[CH:8]([NH:30][C:31]([O:33][CH2:34][CH:35]=[CH2:36])=[O:32])[CH2:9][C:10]1[O:14][N:13]=[C:12]([CH:15]2[CH2:19][CH2:18][CH2:17][N:16]2[C:20](=[O:29])[CH2:21][C:22]2[CH:23]=[CH:24][C:25]([NH:28][C:41](=[O:42])[C:40]3[C:39]([Cl:38])=[CH:47][CH:46]=[CH:45][C:44]=3[Cl:48])=[CH:26][CH:27]=2)[CH:11]=1)[CH3:5]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 783922,6-Dichlorobenzoyl chlorideHCID 20610283HCID 20610283, compound

Product 1

HCID 20610281HCID 20610281, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A dichloromethane (1 mL) solution 2-allyloxycarbonylamino-3-(3-{1-[(4-amino-phenyl)-acetyl]-pyrrolidin-2-yl}-isoxazol-5-yl)-propionic acid ethyl ester (80 mg, 0.170 mmol) was cooled to 0° C. and 2,6-dichlorobenzoylchloride (39 mg, 0.187 mmol) was added. The mixture was stirred for 15 minutes then pyridine (28 μL, 0.34 mmol)was added. The reaction was slowly warmed to room temperature and stirred overnight. The reaction was diluted with ethyl acetate and washed with water, 1 M sodium hydroxide and brine. The organic portion was dried over magnesium sulfate and concentrated to give the title compound (84 mg, 78%). MS (CI) m/z 635.3 (M+1), 632.5 (M−1)

Workup

  1. stirringstirred overnight
  2. washwashed with water, 1 M sodium hydroxide and brine
  3. dry with materialThe organic portion was dried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3c2e39be4e9d49d9a8e3221f968aef8f
Source dataset
uspto-grants-2003_12
Patent number
US06667331B2

Reaction notes

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