Toluene → methyl N-[(3'-cyanobiphenyl-4-yl)sulfonyl]valinate

HRID 606508

반응식

HRID 606508 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([C:16]([O:18][CH3:19])=[O:17])[CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:20]([C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)#[N:21].C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>CCO.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:20]([C:22]1[CH:27]=[C:26]([C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([C:16]([O:18][CH3:19])=[O:17])[CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=2)[CH:25]=[CH:24][CH:23]=1)#[N:21]

참가 물질

8

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 47337186methyl N-[(4-bromophenyl)sulfonyl]-L-valinate

생성물 1

HCID 66769160methyl N-[(3'-cyanobiphenyl-4-yl)sulfonyl]valinate수율 97%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

A suspension of methyl N-[(4-bromophenyl)sulfonyl]valinate obtained in Reference Example 92 (5.00 g, 14.3 mmol), (3-cyanophenyl)boronic acid (2.52 g, 17.1 mmol), tetrakis(triphenylphosphine)palladium (0.330 g, 0.286 mmol) and 2N aqueous sodium carbonate solution (8.57 mL, 17.1 mmol) in EtOH (15 mL)-toluene (50 mL) was heated under reflux for 8 hr under nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was crystallized from hexane-ethyl acetate to give the title compound as a yellow powder (5.18 g, 97%).

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 8 hr under nitrogen atmosphere
  3. washwashed with water and saturated brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was crystallized from hexane-ethyl acetate

출처 및 근거

ORD 기록
ord-8b03e056be9b4eecb0cb5a8f50d27b6a
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915267B2

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