Trifluoroacetic acid → HCID 86755327, compound

HRID 1385805Notes

Reaction equation

HRID 1385805 reaction equation
[C:1]([CH2:4][NH:5][C:6]1[C:7]([I:49])=[C:8]([C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42]([O:44]C(C)(C)C)=[O:43])=[CH:24][CH:23]=2)=[O:20])[C:9]([I:18])=[C:10]([NH:13][CH2:14][C:15](=[O:17])[CH3:16])[C:11]=1[I:12])(=[O:3])[CH3:2].FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1>[C:15]([CH2:14][NH:13][C:10]1[C:9]([I:18])=[C:8]([C:19]([NH:21][C:22]2[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42]([OH:44])=[O:43])=[CH:26][CH:27]=2)=[O:20])[C:7]([I:49])=[C:6]([NH:5][CH2:4][C:1](=[O:3])[CH3:2])[C:11]=1[I:12])(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86755328HCID 86755328, compound

Product 1

HCID 86755327HCID 86755327, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

To a solution of 4-[[[3,5-bis(acetylmethylamino)-2,4,6-triiodophenyl]carbonyl]amino]-benzenepentadecanoic acid, 1.1-dimethylethyl ester XIe of Example 7b (30 mg, 0.3 mmol) in anisole (1 mL), was added trifluoroacetic acid (10 mL) and the mixture stirred at RT overnight (15 h). The solvents were removed in vacuo, and the residue crystallized from ethyl acetate to furnish pure XIIe as a white amorphous solid (205 mg, yield 70%, purity>98%). Additional product (35 mg, purity 96%) was obtained from the mother liquor for a total yield of 81%.

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue crystallized from ethyl acetate
  3. customto furnish pure XIIe as a white amorphous solid (205 mg, yield 70%, purity>98%)
  4. customAdditional product (35 mg, purity 96%) was obtained from the mother liquor for a total yield of 81%

Sources & evidence

ORD record
ord-07d80f1005e442ecaeb2eaea30b1871b
Source dataset
uspto-grants-2001_07
Patent number
US06264916B1

Reaction notes

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