Hydrochloric Acid → HCID 10414610, compound

HRID 1392558Notes

Reaction equation

HRID 1392558 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([Br:15])[C:12]([O:16][C:17]2[CH:22]=[C:21]([CH:23]([CH3:25])[CH3:24])[C:20]([OH:26])=[C:19]([CH2:27][CH3:28])[CH:18]=2)=[C:11]([Br:29])[C:10]=1[CH3:30])=[O:7])C.[Li+].[OH-].Cl>C1COCC1>[Br:29][C:11]1[C:10]([CH3:30])=[C:9]([NH:8][C:6](=[O:7])[CH2:5][C:4]([OH:31])=[O:3])[CH:14]=[C:13]([Br:15])[C:12]=1[O:16][C:17]1[CH:22]=[C:21]([CH:23]([CH3:25])[CH3:24])[C:20]([OH:26])=[C:19]([CH2:27][CH3:28])[CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59678418HCID 59678418, compound

Product 1

HCID 10414610HCID 10414610, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-[3,5-dibromo-4-[3-ethyl-4-hydroxy-5-isopropylphenoxy]-2-methylphenyl]malonamic acid ethyl ester of Part 9D (130 mg, 0.23 mmol) was dissolved in THF (2 mL) and treated with LiOH (2 mL, 1N) for 1 hour at room temperature. The reaction was acidified with 1N HCl and concentrated in vacuo. The remaining water phase was extracted with EtOAc (3×5 mL) and the combined organic phases were dried over Na2SO4 before concentration in vacuo. The residue was purified on column (MPLC, silica gel, gradient elution: CHCl3/MeOH/AcOH from 1:0:0 to 98:2:0.3) to give 50 mg (41%) of N-[3,5-dibromo-4-[3-ethyl-4-hydroxy-5-isopropylphenoxy]-2-methylphenyl]-malonamic acid as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionThe remaining water phase was extracted with EtOAc (3×5 mL)
  3. dry with materialthe combined organic phases were dried over Na2SO4 before concentration in vacuo
  4. customThe residue was purified on column (MPLC, silica gel, gradient elution: CHCl3/MeOH/AcOH from 1:0:0 to 98:2:0.3)

Sources & evidence

ORD record
ord-b2bbd45f24a7484f910d2bea5da21e26
Source dataset
uspto-grants-2008_03
Patent number
US07342127B2

Reaction notes

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