Methyl chloroformate → 5-(3,6-dihydro-4-hydroxy-6-oxo-2-phenyl-2H-pyran-2-yl)pentanoic acid amide
Reaction equation
[OH:1][C:2]1[CH2:3][C:4]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=O)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:5][C:6](=[O:8])[CH:7]=1.C[N:23]1CCOCC1.ClC(OC)=O>C(Cl)Cl>[OH:1][C:2]1[CH2:3][C:4]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]([NH2:23])=[O:21])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:5][C:6](=[O:8])[CH:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a 50 mL reaction flask was added 1.2 mmol of 5-(3,6-dihydro-4-hydroxy-6-oxo-2-phenyl-2H-pyran-2-yl)pentanoic acid (±), 2.4 mmol of 4-methylmorpholine, and 10 mL of CH2Cl2. The reaction was cooled to 0° C. and 2.4 mmol of methyl chloroformate in 3 mL of CH2Cl2 was added. The reaction was stirred at 0° C. for 2 hours. Ammonia was bubbled into the vessel for 10-15 minutes and the reaction allowed to stir for 30 minutes at 0° C. The reaction was poured into ethyl acetate and 1N HCl, the aqueous layer extracted with ethyl acetate, dried over MgSO4, and concentrated. The crude solid was triturated using CH2Cl2 to afford 5-(3,6-dihydro-4-hydroxy-6-oxo-2-phenyl-2H-pyran-2-yl)pentanoic acid amide (±) as a solid (m.p. 173°-174° C.). 1H NMR (DMSO-d6) δ0.8-1.0 (m, 1H), 1.1-1.3 (m, 1H), 1.3-1.5 (m, 2H), 1.8-2.0 (m, 4H), 2.9 (ABq, 2H), 4.8 (s, 1H), 6.6 (s, 1H), 7.2 (s, 1H), 7.2-7.5 (m, 5H), 11.4 (s, 1H).
Workup
- customTo a 50 mL reaction flask
- customAmmonia was bubbled into the vessel for 10-15 minutes
- stirringto stir for 30 minutes at 0° C
- additionThe reaction was poured into ethyl acetate and 1N HCl
- extractionthe aqueous layer extracted with ethyl acetate
- dry with materialdried over MgSO4
- concentrationconcentrated
- customThe crude solid was triturated
Sources & evidence
- ORD record
- ord-6f18fa18955a4aeab5fde72bf1f4aa2f
- Source dataset
- uspto-grants-1998_08
- Patent number
- US05789440
Reaction notes
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