2-Phthalimidoacetaldehyde Diethyl Acetal → Phthalylglycine aldehyde
Reaction equation
C([O:3][CH:4](OCC)[CH2:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16])C>Cl>[O:16]=[C:7]1[C:8]2[C:9](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:11])[N:6]1[CH2:5][CH:4]=[O:3]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
Phthalimidoacetaldehyde diethyl acetal (75 g, 284.8 mmol) was added in one portion to 450 mL of 2N HCl in a 1 L 3-necked round bottom flask equipped with mechanical stirring. The suspension was heated to 70° C. By the time the internal temperature reached 70° C., the reaction mixture was clear and starting material was consumed as determined by HPLC. The reaction mixture was stirred at 70° C. for 30 minutes. The reaction mixture was allowed to cool to ambient temperature with stirring overnight, at which time the solid product had precipitated. The reaction was diluted with 400 mL of water and mixed for 3 hours. The solid was filtered and washed with 1 L of water, air dried, and dried in a vacuum oven at ambient temperature with a nitrogen bleed to afford the title compound (46.5 g, 86.4% yield). 1H NMR (CDCl3): δ 9.65 (s, 1 H), 7.94 (m, 2 H), 7.75 (m, 2 H), 4.58 (s, 2 H).
Workup
- customequipped with mechanical stirring
- customreached 70° C.
- customwas consumed
- temperatureto cool to ambient temperature
- stirringwith stirring overnight, at which time the solid product
- customhad precipitated
- additionThe reaction was diluted with 400 mL of water
- additionmixed for 3 hours
- filtrationThe solid was filtered
- washwashed with 1 L of water, air
- customdried
- customdried in a vacuum oven at ambient temperature with a nitrogen
Sources & evidence
- ORD record
- ord-e9e3c20623554f779435442cf2d3b916
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07834043B2
Reaction notes
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