Triethylamine → HCID 19010158, compound

HRID 1741538Notes

Reaction equation

HRID 1741538 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[NH2:28][C:29]1[CH:30]=[CH:31][C:32]([CH3:36])=[CH:33][C:34]=1[OH:35].C(N(CC)CC)C>CO.C(Cl)(Cl)Cl.CN(C)C=O.C(OCC)(=O)C>[OH:35][C:34]1[CH:33]=[C:32]([CH3:36])[CH:31]=[CH:30][C:29]=1[NH:28][C:10](=[O:12])[CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 760822-Amino-5-methylphenolHCID 78288N-(tert-butoxycarbonyl)glycine

Product 1

HCID 19010158HCID 19010158, compoundYield 29.1%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 21584188Chloroform methanolSolvent

Procedure

To 50 ml of ethyl acetate, there were added 4.27 g (24.4 mmol) of N-(tert-butoxycarbonyl)glycine and 5.03 g (24.4 mmol) of N,N'-dicyclohexyl carbodiimide and stirred at room temperature for 30 minutes. The obtained solution was cooled in an ice bath and 3.00 g (24.4 mmol) of 6-amino-m-cresol and 2.51 g (24.4 mmol) of triethylamine were added thereto. After putting back to room temperature, the mixture was stirred for 12 hours. After the completion of the reaction, 50 ml of N,N-dimethylformamide was added thereto and the crystals thus precipitated were filtered and washed with 20 ml of N,N-dimethylformamide. The filtrate was combined with the washing liquor and the solvent was distilled off therefrom under reduced pressure to thereby give a brown solid. This product was subjected to silica gel column chromatography (Si60 manufactured by Merck; 230-400 mesh; 300 g; eluent: 3% methanol-chloroform). From the 900-1,300 ml fraction, the solvent was distilled off under reduced pressure and 20 ml of chloroform was added thereto to cause thereby crystallization. After filtering and drying, 2.00 g (7.1 mmol) of N-(2-hydroxy-4-methylphenyl)-tert-butoxycarbonylaminoacetamide was obtained as yellow crystals. The yield was 29%.

Workup

  1. temperatureThe obtained solution was cooled in an ice bath
  2. customAfter putting back to room temperature
  3. stirringthe mixture was stirred for 12 hours
  4. additionwas added
  5. customthe crystals thus precipitated
  6. filtrationwere filtered
  7. washwashed with 20 ml of N,N-dimethylformamide
  8. distillationthe solvent was distilled off
  9. customunder reduced pressure to thereby give a brown solid
  10. distillationFrom the 900-1,300 ml fraction, the solvent was distilled off under reduced pressure and 20 ml of chloroform
  11. additionwas added
  12. customcrystallization
  13. filtrationAfter filtering
  14. customdrying

Sources & evidence

ORD record
ord-0ebf32ba58cd4cc98641d916d7b3c854
Source dataset
uspto-grants-1994_08
Patent number
US05334225

Reaction notes

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