Triethylamine → 4-[(2-Nitro-benzenesulfonylamino)-methyl]-benzoic acid tert-butyl ester

HRID 22875

反応式

HRID 22875 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].[C:14]([O:18][C:19](=[O:28])[C:20]1[CH:25]=[CH:24][C:23]([CH2:26][NH2:27])=[CH:22][CH:21]=1)([CH3:17])([CH3:16])[CH3:15].C(N(CC)CC)C>ClCCl>[C:14]([O:18][C:19](=[O:28])[C:20]1[CH:21]=[CH:22][C:23]([CH2:26][NH:27][S:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11])=[CH:24][CH:25]=1)([CH3:17])([CH3:15])[CH3:16]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 14514888tert-Butyl 4-(aminomethyl)benzoate

生成物 1

HCID 697944154-[(2-Nitro-benzenesulfonylamino)-methyl]-benzoic acid tert-butyl ester収率 95.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-Nitro-benzenesulfonyl chloride (8.55 g, 38.6 mmol) and 4-aminomethyl-benzoic acid tert-butyl ester (8.0 g, 38.6 mmol) were mixed in 400 mL of dichloromethane. Triethylamine (10.8 mL, 77.2 mmol) was added, and the resulting mixture was stirred at room temperature for 16 hours. The reaction was partitioned between 1M HCl and dichloromethane. The organic layer was dried (magnesium sulfate), filtered, and rotary evaporated to give 14.46 g (95%) of 4-[(2-nitro-benzenesulfonylamino)-methyl]-benzoic acid tert-butyl ester as an off-white solid. 1H-NMR (CDCl3); δ 8.00 (dd, 1H), 7.84 (m, 3H), 7.67 (m, 2H), 7.27 (dd, 2H), 5.76 (bt, 1H), 4.36 (d, 2H), and 1.57 (s, 9H). MS: M+=392.1 Da Step (2): Synthesis of 4-[(2-Amino-benzenesulfonylamino)-methyl]-benzoic acid tert-butyl ester

後処理

  1. customThe reaction was partitioned between 1M HCl and dichloromethane
  2. dry with materialThe organic layer was dried (magnesium sulfate)
  3. filtrationfiltered
  4. customrotary evaporated

出典と根拠

ORDレコード
ord-4c7eaee1139e429ca701066c340c8244
出典データセット
uspto-grants-2005_02
特許番号
US06849648B2

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