Tert-butyl 4-aminophenethylcarbamate → HCID 178458051, compound

HRID 967834Notes

Reaction equation

HRID 967834 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1.Br.[C:19](SCC1C=CC2C(=CC=CC=2)C=1)(=[NH:22])[CH2:20][CH3:21]>C(O)C>[C:19]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[CH:6][CH:7]=1)(=[NH:22])[CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 382207Tert-butyl 4-aminophenethylcarbamateHCID 222913892-Naphthylmethyl propanimidothioate hydrobromide

Product 1

HCID 178458051HCID 178458051, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of tert-butyl 2-(4-aminophenyl)ethylcarbamate (709 mg, 3 mmol) and 2-naphthylmethyl propanimidothioate hydrobromide (930 mg, 3 mmol) in ethanol (10 mL) was stirred for overnight at ambient temperature. Then, the volatile components were removed by evaporation and the residue was partitioned between diethyl ether (10 mL) and water (10 mL). The aqueous phase was washed with diethyl ether (3×10 mL) and basified by NaOH to pH 10. The aqueous phase was extracted with chloroform (20×4) and the combined extract was dried (MgSO4). Concentration of the organic solvent afforded 831 mg (95%) of the title compound as a colorless powder. MS (ESI) m/z 292 [M+H]+.

Workup

  1. customThen, the volatile components were removed by evaporation
  2. customthe residue was partitioned between diethyl ether (10 mL) and water (10 mL)
  3. washThe aqueous phase was washed with diethyl ether (3×10 mL)
  4. extractionThe aqueous phase was extracted with chloroform (20×4)
  5. extractionthe combined extract
  6. dry with materialwas dried (MgSO4)

Sources & evidence

ORD record
ord-d4eb190a987544438f4deba1a38a8fd6
Source dataset
uspto-grants-2005_10
Patent number
US06956050B2

Reaction notes

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