Tetrahydrofuran → N-[4-(4-Hydroxy-3-isopropyl-phenoxy)-3,5-dimethyl-phenyl]-malonamic acid methyl ester

HRID 432906Notes

Reaction equation

[NH2:1][C:2]1[CH:18]=[C:17]([CH3:19])[C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([CH:14]([CH3:16])[CH3:15])[CH:8]=2)=[C:4]([CH3:20])[CH:3]=1.C(N(CC)CC)C.C[CH:29]([C:33](Cl)=[O:34])[C:30](Cl)=[O:31].C1C[O:39][CH2:38]C1>>[CH3:38][O:39][C:33](=[O:34])[CH2:29][C:30]([NH:1][C:2]1[CH:3]=[C:4]([CH3:20])[C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([CH:14]([CH3:16])[CH3:15])[CH:8]=2)=[C:17]([CH3:19])[CH:18]=1)=[O:31]

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 8471Triethylamine

HCID 10931669Methylmalonylchloride

HCID 121141794-(4-Amino-2,6-dimethyl-phenoxy)-2-isopropyl-phenol

Product 1

HCID 12114180N-[4-(4-Hydroxy-3-isopropyl-phenoxy)-3,5-dimethyl-phenyl]-malonamic acid methyl ester

Procedure

To a solution of 4-(4-amino-2,6-dimethyl-phenoxy)-2-isopropyl-phenol (39 mg, 0.14 mmol) in THF (2 mL) was added triethylamine (22 μL, 0.16 mmol) and methyl malonyl chloride (16 μL, 0.15 mmol). The resulting mixture was stirred at RT for 18 h. The solution was concentrated and the residue was purified by preparative TLC (2.5% MeOH in CH2Cl2) to give the title compound of Step D (31 mg). MS (APCl−) CaIc.: 371.3, Found: 370.3 (M−1).

Workup

concentrationThe solution was concentrated
customthe residue was purified by preparative TLC (2.5% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-ff643fb558604cf2b7b041f67d718325
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06664291B2

Reaction notes

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