Triethylamine → HCID 11340682, compound

HRID 1580868Notes

Reaction equation

HRID 1580868 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].[CH3:15][C:16]([O:19][C:20]([CH2:22][C@H:23]([NH:36][C:37]([O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:38])[C:24](OC1C=CC([N+]([O-])=O)=CC=1)=[O:25])=[O:21])([CH3:18])[CH3:17].C(N(CC)CC)C.C(OCC)(=O)C>CN(C)C=O>[NH:36]([C:37]([O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:38])[C@H:23]([C:24]([NH:6][C@H:5]([C:4]([O:3][CH3:2])=[O:14])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:25])[CH2:22][C:20](=[O:21])[O:19][C:16]([CH3:15])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 156793314-tert-Butyl 1-(4-nitrophenyl) N-[(benzyloxy)carbonyl]-L-aspartate

Product 1

HCID 11340682HCID 11340682, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.0 g of phenylalanine methyl ester hydrochloride together with 6.17 g of Z-Asp(OtBu)-ONP are dissolved in 25 ml of absolute N,N-dimethylformamide to give a clear solution and are mixed with 1.93 ml of triethylamine whilst stirring. The deep yellow solution is stirred overnight at room temperature, is then taken up in a large amount of ethyl acetate, and is washed 3 times with dilute aqueous citric acid solution, 5 times with dilute aqueous soda solution and finally with saturated aqueous sodium chloride solution until the wash liquid remains neutral. After drying over sodium sulphate the solution is evaporated and the resulting oil, which is soluble in ether and in chloroform, is purified by column chromatography on silica gel (the substance is eluted with toluene and toluene/ether, 4 : 1); a colourless oily product is obtained.

Workup

  1. customto give a clear solution
  2. stirringThe deep yellow solution is stirred overnight at room temperature
  3. washis washed 3 times with dilute aqueous citric acid solution, 5 times with dilute aqueous soda solution
  4. dry with materialAfter drying over sodium sulphate the solution
  5. customis evaporated
  6. customis purified by column chromatography on silica gel (the substance
  7. washis eluted with toluene and toluene/ether, 4 : 1)
  8. customa colourless oily product is obtained

Sources & evidence

ORD record
ord-3fa4a72b1cf24920a8b06b3cbcee0cf4
Source dataset
uspto-grants-1976_01
Patent number
US03934008

Reaction notes

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