Water → methyl (S)-2-benzyloxy-3-[3'-(methylamino)biphenyl-4-yl]propanoate

HRID 1865451노트

반응식

HRID 1865451 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[CH3:22][NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26](B2OC(C)(C)C(C)(C)O2)[CH:25]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>CN(C)C=O.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>[CH2:15]([O:14][C@@H:9]([CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([NH:23][CH3:22])[CH:25]=2)=[CH:3][CH:4]=1)[C:10]([O:12][CH3:13])=[O:11])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 57976762N-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 67304959methyl (S)-3-(4-bromophenyl)-2-benzyloxypropanoate

생성물 1

HCID 67305672methyl (S)-2-benzyloxy-3-[3'-(methylamino)biphenyl-4-yl]propanoate수율 63%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

635 mg (0.55 mmol) of tetrakis(triphenylphosphine)palladium are added to a solution of 4 g (11 mmol) of methyl (S)-3-(4-bromophenyl)-2-benzyloxypropionate and 4 g (17 mmol) of methyl[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amine in 25 ml of dimethylformamide. 10 ml of a 2M potassium phosphate solution are added and the reaction mixture is stirred at 70° C. for 1 hour. The reaction is halted by the addition of 50 ml of water and then extraction is carried out with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated and then the residue is chromatographed on silica gel (heptane/ethyl acetate 80/20). 2.6 g of methyl (S)-2-benzyloxy-3-[3′-(methylamino)biphenyl-4-yl]propanoate are obtained in the form of an oil. Yield=61%.

후처리

  1. extractionextraction
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated
  4. customthe residue is chromatographed on silica gel (heptane/ethyl acetate 80/20)

출처 및 근거

ORD 기록
ord-092dd148eec84bee83eea0a2d8162b40
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07626054B2

반응 노트

불러오는 중…