Triethylamine → tert-Butyl (3-{[(2-fluoro-4-nitrophenyl)carbonyl](methyl)amino}propyl)methylcarbamate

HRID 446513

Reaction equation

HRID 446513 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[CH3:28][N:29]([CH2:37][CH2:38][CH2:39][NH:40][CH3:41])[C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33]>C(Cl)Cl>[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([N:40]([CH3:41])[CH2:39][CH2:38][CH2:37][N:29]([CH3:28])[C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:33])[CH3:34])=[O:6]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 3026792-Fluoro-4-nitrobenzoic acidHCID 17868293tert-butyl N-methyl-N-(3-(methylamino)propyl)carbamate

Product 1

HCID 86663428tert-Butyl (3-{[(2-fluoro-4-nitrophenyl)carbonyl](methyl)amino}propyl)methylcarbamateYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Fluoro-4-nitrobenzoic acid (150 mg, 0.810 mmol) was dissolved in methylene chloride (8 mL), triethylamine (0.135 mL, 0.972 mmol) and pivaloyl chloride (0.100 mL, 0.810 mmol) were added under ice cooling, and the mixture was stirred at room temperature for 15 minutes. A solution of tert-butyl methyl[3-(methylamino)propyl]carbamate (described in J. Med. Chem. 1990, 33, 97-101) (164 mg, 0.810 mmol) in methylene chloride (4 mL) was added dropwise under ice cooling, and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and the resulting residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:2→0:100, v/v) to give the title compound (300 mg; yield, 100%) as a yellow oily substance.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. customThe solvent was evaporated under reduced pressure
  3. customthe resulting residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:2→0:100, v/v)

Sources & evidence

ORD record
ord-3ee5d3234b4d49a79e12761e204147d5
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Linked notes

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