Hydrochloric Acid → Ethyl 3-[1,1'-biphenyl]-4-yl-2-[[hydroxy[2-phenyl-1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinyl]methyl]propanoate

HRID 1058768노트

반응식

HRID 1058768 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([CH2:15][P:16]([OH:37])([CH:18]([NH:26][C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[C:38]1(B(O)O)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>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(OCC)(=O)C.C1(C)C=CC=CC=1.CO>[C:2]1([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([CH2:15][P:16]([OH:37])([CH:18]([NH:26][C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 18668696Ethyl 3-(4-bromophenyl)-2-[[hydroxy[2-phenyl-1-[[(phenyl-methoxy)carbonyl]amino]ethyl]phosphinyl]methyl]propanoate

생성물 1

HCID 18668669Ethyl 3-[1,1'-biphenyl]-4-yl-2-[[hydroxy[2-phenyl-1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinyl]methyl]propanoate수율 90.4%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매HCID 21867641Toluene methanol용매

실험 절차

200 mg (0.34 mmol) of ethyl 3-(4-bromophenyl)-2-[[hydroxy[2-phenyl-1-[[(phenyl-methoxy)carbonyl]amino]ethyl]phosphinyl]methyl]propanoate are condensed with 42 mg (0.34 mmol) of phenylboronic acid, working in 1.8 ml of a 2/1 toluene/methanol mixture, tetrakis(triphenylphosphine)palladium and 0.4 ml of 2M sodium carbonate (0.8 mmol). The reaction mixture is stirred for 6 hours under nitrogen and at reflux. After cooling, 10 ml of ethyl acetate are added and the mixture is acidified to pH=3 with aqueous 2N hydrochloric acid solution. After filtration through Celite, rinsed with ethyl acetate, the solvent is evaporated off under reduced pressure. The product is purified by recrystallization from a mixture of ethyl acetate and hexane. 180 mg of product are recovered (yield=90.4%).

후처리

  1. temperatureat reflux
  2. temperatureAfter cooling
  3. filtrationAfter filtration through Celite
  4. washrinsed with ethyl acetate
  5. customthe solvent is evaporated off under reduced pressure
  6. customThe product is purified by recrystallization from a mixture of ethyl acetate and hexane
  7. custom180 mg of product are recovered (yield=90.4%)

출처 및 근거

ORD 기록
ord-1b9c09e4ebac48ef977bbbe3afd9c49c
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06518260B1

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