Methanol → 5-Amino-3-acetoxymethyl-N-(1,3,4-trihydroxybut-2-yl)-2,4,6-triiodobenzamid

HRID 383039

Reaction equation

[NH2:1][C:2]1[C:3]([I:18])=[C:4]([CH2:13][O:14][C:15](=[O:17])[CH3:16])[C:5]([I:12])=[C:6]([C:10]=1[I:11])[C:7](Cl)=[O:8].[NH2:19][CH:20]1[CH2:26][O:25]C(C)(C)[O:23][CH2:22][CH:21]1[OH:29].C(=O)([O-])[O-].[Na+].[Na+].CO>O1CCOCC1.O>[NH2:1][C:2]1[C:3]([I:18])=[C:4]([CH2:13][O:14][C:15](=[O:17])[CH3:16])[C:5]([I:12])=[C:6]([C:10]=1[I:11])[C:7]([NH:19][CH:20]([CH:21]([OH:29])[CH2:22][OH:23])[CH2:26][OH:25])=[O:8]

Participants

Conditions

Temperature: 65 °C

Procedure

5-Amino-3-acetoxymethyl-2,4,6-triiodobenzoyl chloride (12.0 g, 19.8 mmol) was dissolved in dioxane (40 ml). 6-Amino-2,2-dimethyl-1,3-dioxepane-5-ol (3.20 g, 19.8 mmol) and sodium carbonate (2.10 g, 19.8 mmol) were added and the mixture heated to reflux for 10 h. The reaction mixture was cooled, methanol (100 ml) and water (50 ml) were added and the solution was neutralized with a strongly acidic ion exchange resin. The resin was filtered off and a aqueous solution of hydrochloric acid (2M, 20 ml) was added. The mixture was stirred at 60-70° C. for 30 min, and then evaporated to dryness, which gave a semisolid residue (13.6 g) which was used without further purification in the next steps.

Workup

temperaturethe mixture heated
temperatureto reflux for 10 h
temperatureThe reaction mixture was cooled
filtrationThe resin was filtered off
additiona aqueous solution of hydrochloric acid (2M, 20 ml) was added
customevaporated to dryness, which

Sources & evidence

ORD record: ord-06a19f21bf6248c5bfbfe4c139ba6892
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06310243B1

Linked notes

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