Potassium Carbonate → HCID 53747773、化合物

HRID 257555ノート

反応式

HRID 257555 の反応式
[CH3:1][O:2][N:3]=[C:4]([CH2:10][C:11](=[O:16])[CH2:12][CH2:13][CH2:14][CH3:15])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:17]([NH:21][S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]1[CH:36]=[CH:35][C:34]([CH2:37]Br)=[CH:33][CH:32]=1)(=[O:24])=[O:23])([CH3:20])([CH3:19])[CH3:18].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:17]([NH:21][S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH:10]([C:11](=[O:16])[CH2:12][CH2:13][CH2:14][CH3:15])[C:4](=[N:3][O:2][CH3:1])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:33][CH:32]=1)(=[O:24])=[O:23])([CH3:20])([CH3:19])[CH3:18]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 15282100[2'-(N-t-Butylsulfamoyl)biphenyl-4-yl]methyl bromideHCID 53883597HCID 53883597、化合物

生成物 1

HCID 53747773HCID 53747773、化合物収率 71.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 50 mg (0.218 mmol) of ethyl 2-methoxyimino-4-oxooctanoate (from Step A), 83 mg (0.218 mmol) of [2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl bromide (from Step E), 36 mg (0.262 mmol) of freshly pulverized anhydrous potassium carbonate, and 0.6 mL of dry DMF was stirred vigorously for 24 hours at room temperature at which time the starting material was all consumed [TLC (5:1 hexane/EtOAc)]. The mixture was partitioned between 10 mL of EtOAc and 10 mL of 0.2N HCl. The EtOAc layer was then washed with 3×10 mL H2O, 1×5 mL brine, and dried briefly over anhydrous sodium sulfate. The filtrate, obtained from filtration over sintered glass, was concentrated to dryness and the resulting residue was flash chromatographed over 20 mL silica gel (column packed using hexane, sample introduced as a solution in CH2Cl2) eluting with 20/1 hexane/ethyl acetate, to give 83 mg (71%) of the desired product as an oil, homogeneous by TLC. Rf =0.35 in 5:1 hexane/EtOAc. 1H NMR (200 MHz, CDCl3, ppm)=δ0.88 (t, J=7.2 Hz, 3H), 1.00 (s, 9H), 1.31 (m, 5H), 1.52 (m, 2H), 2.32 (t, J=7.0 Hz, 2H), 3.03 (m, 1H), 3.40 (m, 1H), 3.61 (s, 1H), 4.04 (s, 3H), 4.25 (m, 3H), 7.16-7.52 (m, 7H), 8.15 (m, 1H), Mass spectrum: FAB (m/e) 531 (M+1)+.

後処理

  1. customall consumed [TLC (5:1 hexane/EtOAc)]
  2. customThe mixture was partitioned between 10 mL of EtOAc and 10 mL of 0.2N HCl
  3. washThe EtOAc layer was then washed with 3×10 mL H2O, 1×5 mL brine
  4. dry with materialdried briefly over anhydrous sodium sulfate
  5. customThe filtrate, obtained from filtration over sintered glass
  6. concentrationwas concentrated to dryness
  7. customchromatographed over 20 mL silica gel (column
  8. additionintroduced as a solution in CH2Cl2)
  9. washeluting with 20/1 hexane/ethyl acetate

出典と根拠

ORDレコード
ord-0e8a3b7b51df4e6f935291b3c0d1b114
出典データセット
uspto-grants-1993_11
特許番号
US05262412

反応ノート

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