Hydrochloric Acid → HCID 21939845, compound

HRID 1242919Notes

Reaction equation

HRID 1242919 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)(=[O:3])[CH3:2].C(=O)(O)[O-].[Na+].[CH2:19]([O:26][C:27](Cl)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl>C(OCC)(=O)C>[C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:27]([O:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:28])=[CH:11][CH:12]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 141831Benzeneethanol, 4-amino-, acetate (ester)HCID 516892Sodium Bicarbonate

Product 1

HCID 21939845HCID 21939845, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To an ethyl acetate (100 ml) suspension of 4-aminophenylethyl acetate (10 g), saturated aqueous sodium bicarbonate solution (100 ml) was added, and further, benzyloxycarbonyl chloride (12.3 ml) was added dropwise under ice-cooling. After stirring for 1 hour, hydrochloric acid was added to the reaction mixture to make it acidic, and extraction was conducted using ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride solution, dried, and then concentrated. The residue was recrystallized from ethyl acetate-hexane, to give the titled compound (17.3 g).

Workup

  1. additionwas added
  2. temperaturecooling
  3. extractionextraction
  4. washThe organic layer was washed with water and saturated aqueous sodium chloride solution
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-be950aabc2a7412cbbf48857e2fbad3a
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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