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

HRID 22875

반응식

HRID 22875 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-4c7eaee1139e429ca701066c340c8244
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849648B2

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