Triethylamine → 3-[(N-tert-butoxycarbonylamino)acetylaminoj-4-methylaminobenzoic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide

HRID 2288506Notes

Reaction equation

HRID 2288506 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].F[B-](F)(F)F.[CH3:18][N+:19](C)=C(N(C)C)O.C(N(CC)CC)C.[N:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[N:39]([CH2:51][CH2:52][C:53]([O:55][CH2:56][CH3:57])=[O:54])[C:40](=[O:50])[C:41]1[CH:46]=[CH:45][C:44](C)=[C:43]([NH2:48])[C:42]=1N>CN(C)C=O>[N:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[N:39]([CH2:51][CH2:52][C:53]([O:55][CH2:56][CH3:57])=[O:54])[C:40](=[O:50])[C:41]1[CH:46]=[CH:45][C:44]([NH:19][CH3:18])=[C:43]([NH:48][C:10](=[O:12])[CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:42]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 13074157Tetramethyluronium tetrafluoroborateHCID 702875433-amino-4-methyl-amino-benzoic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)-amide

Product 1

HCID 698927693-[(N-tert-butoxycarbonylamino)acetylaminoj-4-methylaminobenzoic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

19.2 g (0.11 mol) of N-tert.butyloxycarbonylglycine were dissolved in 175 ml of dimethylformamide, mixed with 35.2 g (0.11 mol) of O-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate, 11.0 g of triethylamine and 34.2 g (0.10 mol) of 3-amino-4-methyl-amino-benzoic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)-amide and stirred for 2.5 hours at ambient temperature. Then the reaction solution was mixed with 5 l of ice water and stirred for 2 hours. The grey precipitate formed was filtered off, washed with water, dried and recrystallised from ethyl acetate with the addition of activated charcoal. Yield: 39.85 g (80% of theory), C25H33N5O6 (499.6) Rf value: 0.55 (silica gel; methylene chloride/ethanol=19:1)

Workup

  1. stirringstirred for 2 hours
  2. customThe grey precipitate formed
  3. filtrationwas filtered off
  4. washwashed with water
  5. customdried
  6. customrecrystallised from ethyl acetate with the addition of activated charcoal

Sources & evidence

ORD record
ord-71d21173c7b54d85a1a14f1e6e0c013d
Source dataset
uspto-grants-2000_07
Patent number
US06087380

Reaction notes

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