Hydrochloric Acid → HCID 9897385, compound

HRID 1839910Notes

Reaction equation

HRID 1839910 reaction equation
[OH-].[Li+].C([O:10][C:11](=[O:44])[CH2:12][O:13][C:14]1[C:19]([I:20])=[CH:18][C:17]([C:21](=[O:42])[C:22]2[CH:27]=[C:26]([I:28])[C:25]([O:29][CH2:30][C:31]([O:33]CC3C=CC=CC=3)=[O:32])=[C:24]([I:41])[CH:23]=2)=[CH:16][C:15]=1[I:43])C1C=CC=CC=1.Cl>C1COCC1>[C:11]([CH2:12][O:13][C:14]1[C:15]([I:43])=[CH:16][C:17]([C:21]([C:22]2[CH:23]=[C:24]([I:41])[C:25]([O:29][CH2:30][C:31]([OH:33])=[O:32])=[C:26]([I:28])[CH:27]=2)=[O:42])=[CH:18][C:19]=1[I:20])([OH:44])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 9963208HCID 9963208, compound

Product 1

HCID 9897385HCID 9897385, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1.2 M solution of lithium hydroxide (300 μL, 0.36 mmol) was added to a solution of [4-(4-benzyloxycarbonylmethoxy-3,5-diiodo-benzoyl)-2,6-diiodo-phenoxy]-acetic acid benzyl ester (prepared according to Example 12, 76 mg, 0.075 mmol) in 2.4 mL THF. The suspension was stirred for 48 hours, after which time the mixture was poured into 1 M HCl. The resulting white precipitate was isolated by filtration, rinsed with water, and dried in vacuo, yielding the title compound as a white powder (52 mg, 83%). 1H NMR (400 MHz, DMSO-d6): δ 13.17 (br. s, 2H), 8.09 (s, 4H), 4.55 (s, 4H). HPLC (40-90), 10.29 min. LRMS (EI−) calc'd for [C17H10I4O7—H] 832.7, found 832.6.

Workup

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

Sources & evidence

ORD record
ord-d97279f295c746deb6b5359a8308e971
Source dataset
uspto-grants-2004_01
Patent number
US06677473B1

Reaction notes

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