Pyridine → HCID 22397891, compound

HRID 1071278Notes

Reaction equation

HRID 1071278 reaction equation
ClCCl.C([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)C.[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>[CH2:34]([O:33][C:31]([NH:30][CH:8]([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)[C:7]([OH:6])=[O:37])=[O:32])[CH:35]=[CH2:36]

Participants

6

Reactant 4

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

Product 1

HCID 22397891HCID 22397891, compoundYield 80.3%

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, 1M sodium hydroxide and brine. The organic portion was dried over magnesium sulfate and concentrated to give the title compound (84 mg, 78%). MS (Cl) m/z 635.3 (M+1), 632.5 (M−1) C. 2-Allyloxycarbonylamino-3-(3-{1-[(4-amino-phenyl)-acetyl]-pyrrolidin-2-yl}-isoxazol-5-yl)propionic acid ethyl ester

Workup

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

Sources & evidence

ORD record
ord-35cd1ddd26ff4ff0ab21c3c51a31114e
Source dataset
uspto-grants-2005_06
Patent number
US06903128B2

Reaction notes

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