5-(P-tolyl)isoxazole-4-carbonyl chloride → HCID 86617978, compound

HRID 1446326Notes

Reaction equation

HRID 1446326 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[C:13](Cl)=[O:14])=[CH:4][CH:3]=1.[O:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH:18]=[C:17]1[C@@H:25]1[CH2:29][NH:28][CH2:27][C@H:26]1[C:30]([O:32][CH2:33][CH3:34])=[O:31]>ClCCl>[O:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH:18]=[C:17]1[C@@H:25]1[CH2:29][N:28]([C:13]([C:9]2[CH:10]=[N:11][O:12][C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)=[O:14])[CH2:27][C@H:26]1[C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

4

Reactant 2

HCID 729429065-(P-tolyl)isoxazole-4-carbonyl chlorideHCID 86617979HCID 86617979, compound

Product 1

HCID 86617978HCID 86617978, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5-(4-methylphenyl)isoxazole-4-carbonyl chloride (10 mg, 0.045 mmol) in dichloromethane (1 mL) was added ethyl (±)-trans-4-(1-benzofuran-2-yl)pyrrolidine-3-carboxylate (13 mg, 0.050 mmol, 1.1 equ.), and the reaction mixture was stirred for 1 h. The solvent was removed, and the residue was purified by preparative reverse-phase HPLC to give the title compound. HRMS (ESI, pos. ion) m/z calcd for C26H24N2O5: 444.1685, found 444.1693.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-f3d13b1453534bbab5313638cc3f4fca
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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