Tetrahydrofuran → N-[3,5-Dichloro-4-(4-hydroxy-3-nonylcarbamoyl-phenoxy)-phenyl]-malonamic acid methyl ester

HRID 432915Notes

Reaction equation

HRID 432915 reaction equation
[NH2:1][C:2]1[CH:27]=[C:26]([Cl:28])[C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([OH:25])=[C:11]([CH:24]=2)[C:12]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:13])=[C:4]([Cl:29])[CH:3]=1.C[CH:31]([C:35](Cl)=[O:36])[C:32](Cl)=[O:33].C1C[O:41][CH2:40]C1>>[CH3:40][O:41][C:35](=[O:36])[CH2:31][C:32]([NH:1][C:2]1[CH:3]=[C:4]([Cl:29])[C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([OH:25])=[C:11]([C:12](=[O:13])[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:24]=2)=[C:26]([Cl:28])[CH:27]=1)=[O:33]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 10931669MethylmalonylchlorideHCID 223449235-(4-Amino-2,6-dichloro-phenoxy)-2-hydroxy-N-nonyl-benzamide

Product 1

HCID 12114185N-[3,5-Dichloro-4-(4-hydroxy-3-nonylcarbamoyl-phenoxy)-phenyl]-malonamic acid methyl ester

Procedure

To a solution of 5-(4-amino-2,6-dichloro-phenoxy)-2-hydroxy-N-nonyl-benzamide (75 mg, 0.17 mmol) in dry THF (2 ml) at RT was added methyl malonyl chloride (19 μl, 0.18 mmol) with stirring. The resulting mixture was stirred at RT for 2 h then concentrated in vacuo. The residue was purified by preparative TLC (2% MeOH in CH2Cl2) to give the title compound of Step F (78 mg) as a solid. MS (APCl+) Calc.: 538.2, Found: 539.1 (M+1).

Workup

  1. stirringThe resulting mixture was stirred at RT for 2 h
  2. concentrationthen concentrated in vacuo
  3. customThe residue was purified by preparative TLC (2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-185b01cde89b44a592572bbf2cbf5291
Source dataset
uspto-grants-2003_12
Patent number
US06664291B2

Reaction notes

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