Triethylamine → HCID 86757103, compound

HRID 1383732Notes

Reaction equation

HRID 1383732 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][CH:8]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=1)[CH2:9][NH2:10])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:23])[NH:7][CH:8]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=1)[CH2:9][NH:10][C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 86757101HCID 86757101, compound

Product 1

HCID 86757103HCID 86757103, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.53 g (4.75 mmol) of [2-amino-1-[(3-tert-butyl-4-hydroxyphenyl)methyl]ethyl]carbamic acid tert-butyl ester in methylene chloride (20 ml), 0.725 ml (5.23 mmol) of triethylamine and 0.746 ml (5.23 mmol) of benzyl chloroformate were added and the resulting mixture was stirred for 15 minutes. Under cooling with ice, saturated aqueous NaHCO3 was added and the mixture was extracted with methylene chloride and washed with saturated brine. The organic layer was dried with magnesium sulfate and concentrated under reduced pressure; the resulting residue was subjected to silica gel column chromatography (eluting solvent; ethyl acetate:n-hexane=1:1) to give [2-(benzoxycarbonylamino)-1-[(3-tert-butyl-4-hydroxyphenyl)methyl]ethyl]carbamic acid tert-butyl ester in the amount of 1.78 g (82%).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with methylene chloride
  3. washwashed with saturated brine
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washthe resulting residue was subjected to silica gel column chromatography (eluting solvent; ethyl acetate:n-hexane=1:1)

Sources & evidence

ORD record
ord-d5e662a4657043c6bc98ac6a3cb8fb93
Source dataset
uspto-grants-2001_07
Patent number
US06255285B1

Reaction notes

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