Water → HCID 86748394, compound

HRID 1769394Notes

Reaction equation

HRID 1769394 reaction equation
[NH2:1][C:2]1[C:10]([CH2:11]/[CH:12]=[C:13](\[CH3:20])/[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[C:9]([O:21][CH3:22])[C:8]([CH3:23])=[C:7]2[C:3]=1[C:4](=[O:24])[O:5][CH2:6]2.[C:25](N1C=CN=C1)(N1C=CN=C1)=[O:26].O>C(O)=O>[CH:25]([NH:1][C:2]1[C:10]([CH2:11]/[CH:12]=[C:13](\[CH3:20])/[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[C:9]([O:21][CH3:22])[C:8]([CH3:23])=[C:7]2[C:3]=1[C:4](=[O:24])[O:5][CH2:6]2)=[O:26]

Participants

5

Reactant 3

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 86748392HCID 86748392, compound

Product 1

HCID 86748394HCID 86748394, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of methyl (E)-6-(1,3-dihydro-4-amino-6-methoxy-7-methyl-3- oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate (0.32g, 1 mmol) in 3ml formic acid was cooled to 0° C. and treated with 0.45g of carbonyldiimidazole. After 1 hour water was added and the precipitate collected by filtration. This material was recrystallized from isopropanol to give 0.24g of methyl (E)-6-[1,3-dihydro-4-formamido-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl]-4-methyl-4-hexenoate, as a white solid, mp 187°-189° C.

Workup

  1. filtrationthe precipitate collected by filtration
  2. customThis material was recrystallized from isopropanol

Sources & evidence

ORD record
ord-80caac16a5b047edb03fdad9dcf3e6d9
Source dataset
uspto-grants-1995_01
Patent number
US05380879

Reaction notes

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