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

HRID 446513

反応式

HRID 446513 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3ee5d3234b4d49a79e12761e204147d5
出典データセット
uspto-grants-2013_07
特許番号
US08476253B2

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