Tetrahydrofuran → N-[3,5-dibromo-4-[4-hydroxy-3-hydroxymethyl-5-isopropylphenoxy]-2-methylphenyl]malonamic acid ethyl ester

HRID 1392561Notes

Reaction equation

HRID 1392561 reaction equation
[NH2:1][C:2]1[CH:20]=[C:19]([Br:21])[C:5]([O:6][C:7]2[CH:12]=[C:11]([CH:13]([CH3:15])[CH3:14])[C:10]([OH:16])=[C:9]([CH2:17][OH:18])[CH:8]=2)=[C:4]([Br:22])[C:3]=1[CH3:23].C([CH:26]([C:30](Cl)=[O:31])[C:27](Cl)=[O:28])C.CCN(CC)CC.C1C[O:43][CH2:42][CH2:41]1>>[CH2:42]([O:43][C:30](=[O:31])[CH2:26][C:27]([NH:1][C:2]1[CH:20]=[C:19]([Br:21])[C:5]([O:6][C:7]2[CH:12]=[C:11]([CH:13]([CH3:15])[CH3:14])[C:10]([OH:16])=[C:9]([CH2:17][OH:18])[CH:8]=2)=[C:4]([Br:22])[C:3]=1[CH3:23])=[O:28])[CH3:41]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 109209242-Ethylpropanedioyl dichlorideHCID 596784294-(4-Amino-2,6-dibromo-3-methylphenoxy)-2-hydroxymethyl-6-isopropylphenol

Product 1

HCID 59678423N-[3,5-dibromo-4-[4-hydroxy-3-hydroxymethyl-5-isopropylphenoxy]-2-methylphenyl]malonamic acid ethyl esterYield 98%

Procedure

To a stirred solution of 4-(4-amino-2,6-dibromo-3-methylphenoxy)-2-hydroxymethyl-6-isopropylphenol of Part 10B (18 mg, 0.04 mmol), ethylmalonylchloride (5.7 μl, 0.044 mmol) and THF (0.5 mL) was added Et3N (11 μl, 0.08 mmol). After 2 hours stirring at room temperature, the reaction mixture was quenched by NH4Cl (saturated aqueous solution) and the organic phase removed in vacuo. The aqueous phase was extracted with CHCl3 and the resulting two phases were separated with a phase separator (IST). Concentration gave 22 mg (98%) of N-[3,5-dibromo-4-[4-hydroxy-3-hydroxymethyl-5-isopropylphenoxy]-2-methylphenyl]malonamic acid ethyl ester as a yellow foam.

Workup

  1. customthe reaction mixture was quenched by NH4Cl (saturated aqueous solution)
  2. customthe organic phase removed in vacuo
  3. extractionThe aqueous phase was extracted with CHCl3
  4. customthe resulting two phases were separated with a phase separator (IST)
  5. concentrationConcentration

Sources & evidence

ORD record
ord-fcc6d316f5384718b352ffc383e32473
Source dataset
uspto-grants-2008_03
Patent number
US07342127B2

Reaction notes

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