Dansyl chloride → Tert-butyl 3-((3-(3(((5-(dimethylamino)naphthalen-1-yl)(methyl)amino)methyl)phenoxy)propyl)(methyl)amino)-propanoate

HRID 1808728Notes

Reaction equation

HRID 1808728 reaction equation
C([O-])(O)=O.[Na+].[CH3:6][N:7]([CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][NH:28][CH3:29])[CH:22]=1)[CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].S(Cl)([C:33]1[C:45]2[CH:44]=[CH:43][CH:42]=[C:38]([N:39]([CH3:41])[CH3:40])[C:37]=2[CH:36]=[CH:35][CH:34]=1)(=O)=O>O.C(#N)C>[CH3:40][N:39]([CH3:41])[C:38]1[CH:42]=[CH:43][CH:44]=[C:45]2[C:37]=1[CH:36]=[CH:35][CH:34]=[C:33]2[N:28]([CH2:27][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[O:20][CH2:19][CH2:18][CH2:17][N:7]([CH3:6])[CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11])[CH3:29]

Participants

6

Reactant 3

HCID 11801Dansyl chlorideHCID 516892Sodium BicarbonateHCID 59612671Tert-butyl 3-(methyl(3-(3-((methylamino)methyl)phenoxy)propyl)amino)propanoate

Product 1

HCID 67535702Tert-butyl 3-((3-(3(((5-(dimethylamino)naphthalen-1-yl)(methyl)amino)methyl)phenoxy)propyl)(methyl)amino)-propanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

The NaHCO3 solution (133 mg, 1.58 mmol) in water (2 mL) is added at RT to the solution of crude tert-butyl 3-(methyl(3-(3-((methylamino)methyl)phenoxy)propyl)amino)propanoate (455 mg, 1.35 mmol) and of dansyl chloride (364 mg, 1.35 mmol) in acetonitrile (35 mL). This mixture is stirred for 1 h 30 at the same temperature under argon. And the solvent is then evaporated under reduced pressure and the obtained oil is purified by chromatography on silica gel (eluent—DCM followed by the mixture DCM:MeOH=100:1). The final product is obtained as a fluorescent pale green amorphous gum (522 mg, 68%).

Workup

  1. customAnd the solvent is then evaporated under reduced pressure
  2. customthe obtained oil is purified by chromatography on silica gel (eluent—DCM

Sources & evidence

ORD record
ord-59bb72db316d40ca8973fcc3069cda49
Source dataset
uspto-grants-2013_01
Patent number
US08361993B2

Reaction notes

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