Dichloromethane → HCID 66658923, 화합물

HRID 420825노트

반응식

HRID 420825 반응식
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]

참가 물질

9

반응물 4

HCID 6344DichloromethaneHCID 517044Potassium AcetateHCID 59120696HCID 59120696, 화합물HCID 87093775HCID 87093775, 화합물

생성물 1

HCID 66658923HCID 66658923, 화합물수율 74%

시약·촉매·용매 4

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 702Ethanol용매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-dce90cacff3f4f2a981c1fc36d66642b
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08097652B2

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