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

HRID 1058768ノート

反応式

HRID 1058768 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 21867641Toluene methanol溶媒

実験手順

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%).

後処理

  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%)

出典と根拠

ORDレコード
ord-1b9c09e4ebac48ef977bbbe3afd9c49c
出典データセット
uspto-grants-2003_02
特許番号
US06518260B1

反応ノート

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