Hydrochloric Acid → Phthalylglycine aldehyde

HRID 1174115Notes

Reaction equation

HRID 1174115 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>C1COCC1>[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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 3152862-Phthalimidoacetaldehyde Diethyl Acetal

Product 1

HCID 76201Phthalylglycine aldehydeYield 129.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

A solution of phthalimidoacetaldehyde diethyl acetal (39.6 g, 150.4 mmol) in a mixture of THF (80 mL) and aqueous HCl (50 mL, 10%) was heated at 75° C. for 5 hours, cooled to 25° C. and partitioned between ethyl acetate and half-saturated NaHCO3. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated to give the title compound (36.81 g), which was used without further purification.

Workup

  1. temperaturecooled to 25° C.
  2. custompartitioned between ethyl acetate and half-saturated NaHCO3
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2e6a5b3178054aea940448fec081949b
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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