Triethylamine → Coumarin 343 aminohexanoic Acid

HRID 2357107Notes

Reaction equation

HRID 2357107 reaction equation
[CH2:1]1[CH2:21][N:20]2[C:4]3[C:5]([CH2:17][CH2:18][CH2:19]2)=[C:6]2[O:13][C:11](=[O:12])[C:10]([C:14]([OH:16])=[O:15])=[CH:9][C:7]2=[CH:8][C:3]=3[CH2:2]1.C[O:23][C:24](=[O:31])[CH2:25][CH2:26][CH:27](N)[CH2:28][CH3:29].C[N:33](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[CH2:1]1[CH2:21][N:20]2[C:4]3[C:5]([CH2:17][CH2:18][CH2:19]2)=[C:6]2[O:13][C:11](=[O:12])[C:10]([C:14]([OH:16])=[O:15])=[CH:9][C:7]2=[CH:8][C:3]=3[CH2:2]1.[NH2:33][CH:25]([CH2:26][CH2:27][CH2:28][CH3:29])[C:24]([OH:23])=[O:31]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 108770Coumarin 343HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 65440658Methyl 4-aminohexanoate

Product 1

HCID 131728251Coumarin 343 aminohexanoic Acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Coumarin 343 (5 mmol, Aldrich No. 393029) and each 5.5 mmol of 4-aminohexanoic acid methyl ester and HBTU (O-Benzotriazole-N,N,N′,N′-tetramethyl-uronium-hexafluoro-phosphate) as well as 11 mmol triethylamine were dissolved in 100 ml DMF and stirred for 1.5 h at room temperature. The solvent is removed by evaporation on a rotary evaporator and the residuum is dissolved in trichloromethane. Residual HBTU is removed by extraction with water with 0.5 mol/l hydrochloric acid. The organic solvent is separated and evaporated to dryness in a rotary evaporator. The crude product (2.37 g) is purified by flash chromatography (silica gel 60, Merck, No: 11452134001) with a mobile phase consisting of trichloromethane:ethyl acetate 2:1 (v/v) (yield: 1.03 g).

Workup

  1. customThe solvent is removed by evaporation on a rotary evaporator
  2. dissolutionthe residuum is dissolved in trichloromethane
  3. customResidual HBTU is removed by extraction with water with 0.5 mol/l hydrochloric acid
  4. customThe organic solvent is separated
  5. customevaporated to dryness in a rotary evaporator
  6. customThe crude product (2.37 g) is purified by flash chromatography (silica gel 60, Merck

Sources & evidence

ORD record
ord-1b12e1dc49ff4ee7b915ed13ef1817a5
Source dataset
uspto-grants-2010_07
Patent number
US07759470B2

Reaction notes

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