Triethylamine → HCID 178501401, compound

HRID 1608442Notes

Reaction equation

HRID 1608442 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][CH:5]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[F:16])[C:6]([OH:8])=O.Cl.Cl.[CH3:23][O:24][C:25](=[O:34])[C@H:26]([CH2:28][C:29]1[N:33]=[CH:32][NH:31][CH:30]=1)[NH2:27].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O>[CH3:23][O:24][C:25](=[O:34])[C@H:26]([CH2:28][C:29]1[N:33]=[CH:32][NH:31][CH:30]=1)[NH:27][C:6](=[O:8])[CH:5]([CH2:4][C:3]1[CH:17]=[CH:18][CH:19]=[CH:20][C:2]=1[F:1])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[F:16]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 18957612HCID 18957612, compoundHCID 178419105HCID 178419105, compound

Product 1

HCID 178501401HCID 178501401, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 30 ml of N,N-dimethylformamide were suspended 1.8 g of bis(2-fluorobenzyl)acetic acid and 1.9 g of L-histidine methyl ester dihydrochloride, and to the suspension were successively added 1.68 ml of diphenylphosphoryl azide and 2.9 ml of triethylamine with stirring under ice-cooling. The mixture was still stirred for 16 hours. The reaction mixture was evaporated under reduced pressure, and to the residue was added a 5% aqueous sodium bicarbonate solution. The mixture was extracted with ethyl acetate, and the ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=1) to obtain 2.0 g of N- bis(2-fluorobenzyl)acetyl-L-histidine methyl ester having an Rf1 value of 0.76 as a white powder.

Workup

  1. temperaturecooling
  2. stirringThe mixture was still stirred for 16 hours
  3. customThe reaction mixture was evaporated under reduced pressure
  4. additionto the residue was added a 5% aqueous sodium bicarbonate solution
  5. extractionThe mixture was extracted with ethyl acetate
  6. washthe ethyl acetate layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=1)

Sources & evidence

ORD record
ord-5a768de7cdba420789b004d3f4960040
Source dataset
uspto-grants-1989_09
Patent number
US04870183

Reaction notes

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