Triethylamine → Coumarin 343 aminopropionic Acid-tert-butyl Ester

HRID 2357109Notes

Reaction equation

HRID 2357109 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:22]([O:26][C:27](=[O:31])[CH:28]([NH2:30])[CH3:29])([CH3:25])([CH3:24])[CH3:23].CN(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.[C:22]([O:26][C:27](=[O:31])[CH:28]([NH2:30])[CH3:29])([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 108770Coumarin 343HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 4351123Tert-butyl 2-aminopropanoate

Product 1

HCID 131728253Coumarin 343 aminopropionic Acid-tert-butyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

285 mg Coumarin 343 (1 mmol), 262 mg aminopropionic acid tert. butyl ester (1.2 mmol) and 343 mg HBTU (1.2 mmol) were dissolved in 5 ml of dry DMF. 280 μl triethylamine were added and the solution was stirred for 2 hours at room temperature. The solvent was evaporated in a vacuum on a rotary evaporator and the product was purified by column chromatography (silica gel 60, Merck, mobile phase: ethyl acetate/methanol 2:1 (v/v)).

Workup

  1. customThe solvent was evaporated in a vacuum on a rotary evaporator
  2. customthe product was purified by column chromatography (silica gel 60, Merck, mobile phase: ethyl acetate/methanol 2:1 (v/v))

Sources & evidence

ORD record
ord-ca2a4478b5ce461999417b4c3f8ac248
Source dataset
uspto-grants-2010_07
Patent number
US07759470B2

Reaction notes

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