Triethylamine → HCID 178453621, compound

HRID 1031745Notes

Reaction equation

HRID 1031745 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:21]([CH2:24][CH3:25])CC)C>ClCCl>[C:1]([O:5][C:6]([NH:8][CH2:9][C@H:10]1[CH2:11][CH2:12][C@H:13]([C:14]([NH:8][C:6](=[O:5])[C@H:24]([CH2:25][C:10]2[CH:18]=[CH:17][CH:13]=[CH:12][CH:11]=2)[NH2:21])=[O:16])[CH2:17][CH2:18]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 8536054-(((tert-Butoxycarbonyl)amino)methyl)benzoic acid

Product 1

HCID 178453621HCID 178453621, compoundYield 145.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-(t-butoxycarbonylaminomethyl)benzoic acid (3.77 g), L-phenylalamine amide hydrochloride (3.01 g), triethylamine (2.25 g) and dry dichloromethane (100 ml) 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (3.16 g) was added, under ice-cooling, and after cooling for 2 hours, the mixture was stirred under room temperature for 2 hours. The solvent was evaporated under a reduced pressure, water was added to the residue to effect powdering, and the powder was collected by filtration. The powder was washed with 10% aqueous citric acid, water, 5% aqueous sodium hydrogen carbonate, and then water, in this order, followed by drying, to give N-[4-(t-butoxycarbonylaminomethyl)benzoyl]-L-phenylalamine amide (I) (4.41 g). The structure was confirmed by NMR spectrum.

Workup

  1. additionwas added, under ice-
  2. temperaturecooling
  3. temperatureafter cooling for 2 hours
  4. customThe solvent was evaporated under a reduced pressure, water
  5. additionwas added to the residue to effect powdering
  6. filtrationthe powder was collected by filtration
  7. washThe powder was washed with 10% aqueous citric acid, water, 5% aqueous sodium hydrogen carbonate
  8. customby drying

Sources & evidence

ORD record
ord-cad5ce444ef94dcca8029c54fd7dedeb
Source dataset
uspto-grants-1990_09
Patent number
US04954512

Reaction notes

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