Methanol → HCID 59411473, compound
Reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7]O[C:9]2=[O:14])([O-:3])=[O:2].[NH2:15][C:16]([CH3:20])([CH3:19])[CH2:17][OH:18].C[OH:22].C(N([CH2:28][CH3:29])CC)C>>[C:28]([O:18][CH2:17][C:16]([CH3:20])([N:15]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[CH:13][C:4]=2[N+:1]([O-:3])=[O:2])[C:9]1=[O:14])[CH3:19])(=[O:22])[CH3:29]Participants
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 5-nitro-isochromen-1-one (1.02 g, 0.00480 mol), 2-amino-2-methyl-1-propanol (0.921 mL, 0.00960 mol) and methanol (23 mL, 0.58 mol) and triethylamine (2 mL, 0.01 mol) was stirred overnight at 80° C. LC-MS analysis showed the formation of the desired product. Volatiles were removed under reduced pressure and the residue was taken up in a mixture of methylene chloride (20 mL, 0.3 mol) and N,N-dimethylformamide (0.85 mL, 0.011 mol). Acetyl chloride (1.0 mL, 0.014 mol) and N,N-diisopropylethylamine (1.5 mL, 0.0088 mol) were added. The mixture was allowed to stir at 40° C. for 5 hours. The flask was cooled to room temperature and solvents were removed in vacuo. The residue was taken up in Ethyl acetate and washed twice with aqueous NaHCO3. The organic layer was dried with Sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography using an Ethyl acetate: Hexane (0-100%) gradient to obtain the desired product. M+1=263.2
Sources & evidence
- ORD record
- ord-b4764536f13f4762852a5c902091b4e0
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07816371B2
Reaction notes
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