Hydrochloric Acid → Phthalylglycine aldehyde

HRID 243588

Reaction equation

HRID 243588 reaction equation
C(O[C:4]1([O:14]CC)[NH:8][C:7](=[O:9])[C:6]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:5]12)C.Cl.[C:18](OCC)(=[O:20])[CH3:19]>O1CCCC1>[O:14]=[C:4]1[C:5]2[C:6](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:7](=[O:9])[N:8]1[CH2:19][CH:18]=[O:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 66899166Phthalimide diethylacetal

Product 1

HCID 76201Phthalylglycine aldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of phthalimide diethylacetal (15 g) in tetrahydrofuran (THF) (30 mL) was added 10% aqueous HCl (18 mL). After heating at 75° C. for 5 hrs, the solution was allowed to cool to RT, and ethyl acetate (100 mL) was added. The solution was extracted with saturated sodium carbonate solution (100 mL), brine (100 mL), and the organic layer was separated and dried over magnesium sulfate (MgSO4). The solution was filtered and evaporated to provide 11.2 g of the titled compound.

Workup

  1. temperatureto cool to RT
  2. extractionThe solution was extracted with saturated sodium carbonate solution (100 mL), brine (100 mL)
  3. customthe organic layer was separated
  4. dry with materialdried over magnesium sulfate (MgSO4)
  5. filtrationThe solution was filtered
  6. customevaporated

Sources & evidence

ORD record
ord-7c1115ba6deb4bdea03b4f40c87e0f17
Source dataset
uspto-grants-2014_02
Patent number
US08653141B2

Linked notes

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