Triethylamine → 4-{4-[Bis(methanesulfonyl)amino]phenyl}butylcarbamic acid tert-butyl ester

HRID 889863ノート

反応式

HRID 889863 の反応式
[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>C1COCC1.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([N:18]([S:28]([CH3:27])(=[O:30])=[O:29])[S:28]([CH3:27])(=[O:30])=[O:29])=[CH:16][CH:17]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11558019[4-(4-Aminophenyl)butyl]carbamic acid tert-butyl ester

生成物 1

HCID 668495244-{4-[Bis(methanesulfonyl)amino]phenyl}butylcarbamic acid tert-butyl ester収率 83%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

Compound 52 (0.16 g, 0.605 mmol) was dissolved in anhydrous THF (5 mL). To the clear solution were sequentially added triethylamine (0.18 mL, 1.21 mmol) and 4-dimethylaminopyridine (15 mg, 0.121 mmol). The mixture was cooled to about −10° C. for 15 min by a methanol-ice bath. To the cold solution was slowly added methanesulfonyl chloride (51 μL). The solution was further stirred at the temperature (about −10° C.) for an additional 30 min, then allowed to slowly warm up to room temperature by removing the cooling bath. The reaction mixture was concentrated under reduced pressure. The residue was chromatographed over silica gel, eluting with a mixture of ethyl acetate (0–35%) and hexanes (100–65%), to afford 0.212 g (83%) of the product 53 as a white solid. 1H NMR (CDCl3) δ 1.44 (s, 9H), 1.52–1.70 (m, 4H), 2.68 (t, J=7.4 Hz, 2H), 3.13–3.18 (m, 2H), 3.40 (s, 6H), 4.53 (br s, 1H), 7.27 (s, 4H). m/z (APCI)=321 [C17H28N2O6S2-Boc+H]+.

後処理

  1. temperatureto slowly warm up to room temperature
  2. customby removing the cooling bath
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe residue was chromatographed over silica gel
  5. washeluting with a mixture of ethyl acetate (0–35%) and hexanes (100–65%)

出典と根拠

ORDレコード
ord-f42eb2c51eac45859c4f3b13339fea49
出典データセット
uspto-grants-2006_02
特許番号
US06995160B2

反応ノート

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