Dichloromethane → HCID 66658923、化合物

HRID 420825ノート

反応式

HRID 420825 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]([CH3:24])[CH2:16][NH:17][S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])=[CH:11][CH:10]=2)O1.[C:26]([C:28]1[CH:29]=[C:30]([CH:36]=[CH:37][C:38]=1OS(C(F)(F)F)(=O)=O)[C:31]([O:33][CH2:34][CH3:35])=[O:32])#[N:27].C(Cl)Cl.CC([O-])=O.[K+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O.CCO>[C:26]([C:28]1[CH:29]=[C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:36]=[CH:37][C:38]=1[C:9]1[CH:10]=[CH:11][C:12]([C@H:15]([CH3:24])[CH2:16][NH:17][S:18]([CH:21]([CH3:22])[CH3:23])(=[O:19])=[O:20])=[CH:13][CH:14]=1)#[N:27]

参加物

9

反応物 4

HCID 6344DichloromethaneHCID 517044Potassium AcetateHCID 59120696HCID 59120696、化合物HCID 87093775HCID 87093775、化合物

生成物 1

HCID 66658923HCID 66658923、化合物収率 74%

試薬・触媒・溶媒 4

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

Stir a solution of (2R)-propane-2-sulfonic acid {2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-amide (50 g, 136.2 mmol), Ethyl 3-Cyano-4-trifluoromethanesulfonyloxy-benzoate (40 g, 123.8 mmol), PdCl2(dppf).DCM (3.03 g, 3.71 mmol) and KOAc (36.43 g, 371.4 mmol) in DME:EtOH:H2O (200 mL/200 mL/200 mL) under nitrogen at 80° C. for 50 minutes. Pour the reaction mixture into ice-water and extract it with EtOAc. Wash the organic layer with water and saturated aq. sodium chloride solution, dry over MgSO4, filter and concentrate it in vacuo. Subject residue to silica gel chromatography eluting with hexane/EtOAc 4:1 to 3:1. Triturate the product in hexane, filter and dry, to yield 37.95 g of 1-(S)-Ethyl 2-Cyano-4′-[1-methyl-2-(propane-2-sulfonylamino)-ethyl]-biphenyl-4-carboxylate (74%). MS(ES): m/z=413.1 [M-H].

後処理

  1. extractionextract it with EtOAc
  2. washWash the organic layer with water and saturated aq. sodium chloride solution
  3. dry with materialdry over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate it in vacuo
  6. washSubject residue to silica gel chromatography eluting with hexane/EtOAc 4:1 to 3:1
  7. customTriturate the product in hexane
  8. filtrationfilter
  9. customdry

出典と根拠

ORDレコード
ord-dce90cacff3f4f2a981c1fc36d66642b
出典データセット
uspto-grants-2012_01
特許番号
US08097652B2

反応ノート

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