4-Toluenesulfonyl chloride → Ethyl 4-(4-(4-methylphenylsulfonamido)-3-phenylbutanamido)benzoate

HRID 2422943노트

반응식

HRID 2422943 반응식
C(=O)([O-])[O-].[K+].[K+].[NH2:7][CH2:8][CH:9]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:10][C:11]([NH:13][C:14]1[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=1)=[O:12].[S:31](Cl)([C:34]1[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=1)(=[O:33])=[O:32]>O1CCOCC1.O>[CH3:38][C:37]1[CH:39]=[CH:40][C:34]([S:31]([NH:7][CH2:8][CH:9]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:10][C:11]([NH:13][C:14]2[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=2)=[O:12])(=[O:33])=[O:32])=[CH:35][CH:36]=1

참가 물질

5

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 67243563Ethyl 4-(4-amino-3-phenylbutanamido)benzoate

생성물 1

HCID 24786212Ethyl 4-(4-(4-methylphenylsulfonamido)-3-phenylbutanamido)benzoate수율 65%

시약·촉매·용매 1

HCID 218864351,4-Dioxane--water (1/1)용매

실험 절차

Potassium carbonate (0.325 g, 2.35 mmol) was added to a solution of 51 (0.128 g, 0.392 mmol) in 1,4-dioxane/H2O 1:1 (5 mL) and followed by tosyl chloride (0.074 g, 0.392 mmol) at room temperature. After stirring for 2 h at room temperature, the resulting mixture was evaporated in vacuo to dryness. Water (10 ml) was added and the resulting white solid was separated by filtration and dried in vacuo. Pure 55 was obtained as an off-white solid (0.122 g, 0.254 mmol, 65%) without further purification, mp 135-137° C. 1H NMR (400 MHz, CD3OD) 1.36 (3H, t, J 7.2 Hz), 2.39 (3H, s), 2.63 (1H, dd, J 8.6, 14.6 Hz), 2.85 (1H, dd, J 6.2, 15.0 Hz), 3.05 (1H, dd, J 7.4, 13.0 Hz), 3.12 (1H, dd, J 6.8, 11.8 Hz), 4.32 (2H, q, J 7.2 Hz), 7.17-7.19 (3H, m), 7.23-7.27 (2H, m), 7.31 (2H, d, J 8.0 Hz), 7.54 (2H, d, J 8.4 Hz), 7.65 (2H, d, J 8.4 Hz), 7.90 (2H, d, J 8.8 Hz). 13C NMR (100 MHz, CDCl3) 14.57, 21.73, 40.65, 42.04, 47.77, 61.07, 119.15, 127.14, 127.75, 127.77, 129.29, 130.07, 130.94, 136.79, 140.74, 142.12, 143.97, 166.36, 170.24. νmax (solid)/(cm−1) 3324, 3191, 1707, 1675, 1597, 1534, 1270, 1157, 1105. MS (API-ES): m/z 481 [M+H]+ (100%), HRMS (API-ES) m/z found 481.1801 [M+H]+.

후처리

  1. customthe resulting mixture was evaporated in vacuo to dryness
  2. additionWater (10 ml) was added
  3. customthe resulting white solid was separated by filtration
  4. customdried in vacuo

출처 및 근거

ORD 기록
ord-b4eb34366d934c2caef78182809b1022
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960434B2

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