Formaldehyde → t-Butyl 4-(succinimidomethylamino)phenoxyacetate

HRID 1290983Notes

Reaction equation

HRID 1290983 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[CH:4][CH:3]=1.[C:17]1(=[O:23])[NH:21][C:20](=[O:22])[CH2:19][CH2:18]1.[CH2:24]=O>C(O)C>[C:20]1(=[O:22])[N:21]([CH2:24][NH:1][C:2]2[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])=[CH:15][CH:16]=2)[C:17](=[O:23])[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 11439SuccinimideHCID 22060435Tert-butyl 2-(4-aminophenoxy)acetate

Product 1

HCID 10616705t-Butyl 4-(succinimidomethylamino)phenoxyacetateYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

t-Butyl 4-aminophenoxyacetate (7.00 g, 31.4 mmol) and succinimide (3.11 g, 31.4 mmol) were added to ethanol (40 ml), and a 37% aqueous formaldehyde solution (2.55 g, 31.4 mmol) was added. The mixtue was refluxed under heating for 4 hours. Low boiling matters were distilled away from the reaction mixture under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate) to give 8.37 g of t-butyl 4-(succinimidomethylamino)phenoxyacetate as a yellow solid (84%). This solid (8.30 g, 26.0 mmol) was dissolved in dimethyl sulfoxide (50 ml) and sodium borohydride (989 mg, 26.0 mmol) was added, which was followed by stirring at 100° C. for 30 minutes. After cooling, water was poured into the reaction mixture and the mixture was extracted with diethyl ether. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. After filtration, low boiling matters were distilled away from the filtrate under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1) to give 3.62 g of t-butyl 4-(methylamino)phenoxyacetate as a yellow oil (59%).

Workup

  1. temperatureThe mixtue was refluxed
  2. temperatureunder heating for 4 hours
  3. distillationwere distilled away from the reaction mixture under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-ab375f6607914d07926bd25231293dde
Source dataset
uspto-grants-1998_05
Patent number
US05753670

Reaction notes

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