Water → [3,5,3'',5''-Tetramethyl-5'-(8-phenyl-octylcarbamoyl)-[1,1':3',1'']terphenyl-2'-yloxy]acetic Acid

HRID 324089ノート

反応式

HRID 324089 の反応式
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:43])[C:17]2[CH:22]=[C:21]([C:23]3[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[CH:24]=3)[C:20]([O:31][CH2:32][CH2:33][OH:34])=[C:19]([C:35]3[CH:40]=[C:39]([CH3:41])[CH:38]=[C:37]([CH3:42])[CH:36]=3)[CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[N+]1([O-])CC[O:48]CC1.O.S(=O)(O)[O-].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(#N)C.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O.CC(O)=O.CCOC(C)=O>[CH3:29][C:27]1[CH:28]=[C:23]([C:21]2[CH:22]=[C:17]([C:16](=[O:43])[NH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:18]=[C:19]([C:35]3[CH:40]=[C:39]([CH3:41])[CH:38]=[C:37]([CH3:42])[CH:36]=3)[C:20]=2[O:31][CH2:32][C:33]([OH:48])=[O:34])[CH:24]=[C:25]([CH3:30])[CH:26]=1

参加物

9

反応物 4

HCID 962WaterHCID 82029Methyl morpholine oxide3 回HCID 22237505N-8-Phenyloctyl-3,5-bis-(3,5-dimethylphenyl)-4-(2-hydroxyethoxy)benzamideHCID 86583660Sodium bisulfite sodium dithionite

生成物 1

HCID 9873259[3,5,3'',5''-Tetramethyl-5'-(8-phenyl-octylcarbamoyl)-[1,1':3',1'']terphenyl-2'-yloxy]acetic Acid収率 23%

試薬・触媒・溶媒 4

HCID 178419074HCID 178419074、化合物触媒2 回HCID 176Acetic Acid溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of N-8-phenyloctyl-3,5-bis-(3,5-dimethylphenyl)-4-(2-hydroxyethoxy)benzamide (850 mg, 1.47 mmol) in 15 mL of acetonitrile was added NMMO (415 mg, 3.05 mmol) and TPAP (52 mg, 0.149 mmol). The reaction was stirred for 2 hours then an additional 40 mg, 0.3 mmol NMMO and 52 mg, 0.149 mmol TPAP were added. The reaction was stirred overnight and an additional 40 mg, 0.3 mmol, NMMO was added. The reaction was stirred an additional two hours then water was added followed by the addition of sodium bisulfite/sodium dithionite. The aqueous mixture was stirred for 1 hour then it was extracted with EtOAc (3×). The combined extracts were dried with Na2SO4 and concentrated to give a black oil. This oil was subjected to flash chromatography (20%EtOAc:80% Hexanes acidified with 1% CH3COOH) on HCOOH pretreated silica gel. There yielded 200 mg of the desired acid plus a fraction consisting of the desired acid and other impurities. This fraction was chromatographed again using the same solvent system to give 30 mg more of the acid for a total yield of 230 mg, 26.4% of the desired acid. 1H NMR (DMSO-d6) δ1.27 (bs, 8H); 1.45-1.60 (m, 4H); 2.31 (s, 12H); 2.53 (t, J=7.58 Hz, 2H); 3.23 (quartet, J=6.37 Hz, 2H); 3.81 (s, 2H); 7.00-7.01 (m, 2H); 7.13-7.15 (m, 3H); 7.19-7.25 (m, 6H); 7.76 (s, 2H); 8.48 (t, J=6.00 Hz, 1H); 12.35 (bs, 1H); IR 3325, 2935, 2875, 1750, 1645, 1605, 1580, 1545, 1480, 1460, 1430, 1400, 1385, 1380, 1295, 1250, 1200, 1150, 850, and 700 cm−1; mass spectrum [(+)APCI], m/z 592 [M+H]+; Anal Calcd for C39H45NO4.C2H4O2.C4H8O2: C, 73.03; 7.63; H, 7.63; N, 1.89; Found: C, 73.32, FE, 7.88; N, 2.04.

後処理

  1. stirringThe reaction was stirred overnight
  2. stirringThe reaction was stirred an additional two hours
  3. stirringThe aqueous mixture was stirred for 1 hour
  4. extractionit was extracted with EtOAc (3×)
  5. dry with materialThe combined extracts were dried with Na2SO4
  6. concentrationconcentrated
  7. customto give a black oil

出典と根拠

ORDレコード
ord-dc12dfdea60c4821904322896b01e14a
出典データセット
uspto-grants-2001_04
特許番号
US06214877B1

反応ノート

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