Hydrochloric Acid → HCID 9939186, compound

HRID 989414Notes

Reaction equation

HRID 989414 reaction equation
[Li+].[OH-].IC1C=C(C=CC=1)C[O:8][C:9](=[O:29])[CH2:10][CH2:11][C:12]1[CH:17]=[C:16]([I:18])[C:15]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([I:27])[CH:22]=2)=[C:14]([I:28])[CH:13]=1.Cl.CO>C1COCC1>[I:18][C:16]1[CH:17]=[C:12]([CH2:11][CH2:10][C:9]([OH:29])=[O:8])[CH:13]=[C:14]([I:28])[C:15]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([I:27])[CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 9897455HCID 9897455, compound

Product 1

HCID 9939186HCID 9939186, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1.2 M solution of LiOH (275 μL, 0.33 mmol) was added to a solution of 3-(3,5-diiodo-4-(3-iodobenzyloxy)phenyl)propionic acid 3-iodobenzyl ester (Example 3)(213 mg, 0.25 mmol) in 2 mL THF. The biphasic solution was stirred for 14 hours, then 6 mL 0.5 M HCl was added and an oil formed. Methanol (0.5 mL) was added and the oil formed a solid, which was removed by filtration, yielding the title compound as an off-white powder (150 mg, 95%); 1H NMR (DMSO) δ 12.15 (s, 1H), 7.96 (s, 1H), 7.76-7.75 (m, 3H), 7.62 (d, J=7.6 Hz, 1H), 7.26 (t, J=7.6 Hz, 1H), 4.87 (s, 2H), 2.75 (t, J=7.2 Hz, 2H), 2.54 (t, J=7.4 Hz).

Workup

  1. customan oil formed
  2. customthe oil formed a solid, which
  3. customwas removed by filtration

Sources & evidence

ORD record
ord-7d6b12abfec344cda283ab89632a508a
Source dataset
uspto-grants-2003_10
Patent number
US06638977B1

Reaction notes

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