Hydrochloric Acid → HCID 23450780, compound

HRID 1839909Notes

Reaction equation

HRID 1839909 reaction equation
[OH-].[Li+].C([O:10][C:11](=[O:33])[CH2:12][O:13][C:14]1[C:19]([I:20])=[CH:18][C:17]([C:21](=[O:31])[C:22]2[CH:27]=[C:26]([I:28])[C:25]([OH:29])=[C:24]([I:30])[CH:23]=2)=[CH:16][C:15]=1[I:32])C1C=CC=CC=1.Cl>C1COCC1>[OH:29][C:25]1[C:24]([I:30])=[CH:23][C:22]([C:21]([C:17]2[CH:16]=[C:15]([I:32])[C:14]([O:13][CH2:12][C:11]([OH:33])=[O:10])=[C:19]([I:20])[CH:18]=2)=[O:31])=[CH:27][C:26]=1[I:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 9811363HCID 9811363, compound

Product 1

HCID 23450780HCID 23450780, compoundYield 125.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1.2 M solution of lithium hydroxide (100pL, 0.12 mmol) was added to a solution of [4-(4-hydroxy-3,5-diiodobenzoyl)-2,6-diiodo-phenoxy]-acetic acid benzyl ester (prepared according to Example 10, 50 mg, 0.043 mmol) in 1 mL THF. The biphasic solution was stirred for 6 hours, after which time 1 M HCl was added. The resulting white precipitate was isolated by filtration, rinsed with water, and dried in vacuo, yielding the title compound as a white powder (42 mg, 94%). 1H NMR (400 MHz, DMSO-d6): δ 13.18 (br. s, 1H), 10.57 (br. s, 1H), 8.06 (s, 2H), 8.03 (s, 2H), 4.55 (s, 2H). HPLC (40-90), 12.41 min. LRMS (EI−) calc'd for [C15H8I4O5—H] 744.6, found 744.8.

Workup

  1. customThe resulting white precipitate was isolated by filtration
  2. washrinsed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-3d42d99346064dd1870dc00021f1e6c7
Source dataset
uspto-grants-2004_01
Patent number
US06677473B1

Reaction notes

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