4-Toluenesulfonyl chloride → HCID 178483172, 화합물

HRID 1797128노트

반응식

HRID 1797128 반응식
[C:1]1([CH:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:8][N:9]([CH3:20])[C:10](=[O:19])[CH:11](O)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[NH2:40][CH2:41][CH2:42][C:43]1[N:47]=[CH:46][NH:45][CH:44]=1>O1CCCC1.CO>[C:1]1([CH:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:8][N:9]([CH3:20])[C:10](=[O:19])[CH:11]([NH:40][CH2:41][CH2:42][C:43]2[N:47]=[CH:46][NH:45][CH:44]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 4

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 22174856N-(2,2-Diphenyl-ethyl)-2-hydroxy-N-methyl-2-phenyl-acetamideHCID 178419017HCID 178419017, 화합물

생성물 1

HCID 178483172HCID 178483172, 화합물수율 57%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To stirred solution of the product of step 1 (1.50 g, 4.34 mmol) in tetrahydrofuran (15 mL) was added a 60% dispersion of sodium hydride in mineral oil (0.210 g, 5.25 mmol). After gas evolution ceased, p-toluenesulfonyl chloride (0.990 g, 5.20 mmol) was added and the mixture was stirred for 2 hours. At this time, histamine (1.93 g, 17.4 mmol) was added followed by methanol (10 mL). The reaction was stirred overnight and concentrated. The residue was partitioned between ethyl acetate and aqueous sodium carbonate solution. The organic layer was dried (sodium sulfate) and concentrated to afford a pasty white solid. Flash chromatography over silica (methylene chloride/methanolic ammonia solution) provided 1.08 g (57%) of product as a colorless tacky foam: 1H NMR (CDCl3) δ 7.52–7.43 (m, 1H), 7.40–7.00 (m, 15H), 6.78–6.69 (m, 1H), 4.36–3.97 (m, 4H), 2.92–2.20 (m, 7H) ppm.

후처리

  1. stirringThe reaction was stirred overnight
  2. concentrationconcentrated
  3. customThe residue was partitioned between ethyl acetate and aqueous sodium carbonate solution
  4. dry with materialThe organic layer was dried (sodium sulfate)
  5. concentrationconcentrated
  6. customto afford a pasty white solid

출처 및 근거

ORD 기록
ord-fff33542f648433dbcab01f96252520b
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07034031B2

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