Tri-o-tolylphosphine → Ammonia

HRID 1433284ノート

反応式

HRID 1433284 の反応式
[CH2:1]([N:9]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8].[CH2:24]([O:31][C:32]1[CH:37]=[CH:36][C:35](Br)=[CH:34][C:33]=1[C@@H:39]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[CH2:40][CH2:41][N:42]([CH:46]([CH3:48])[CH3:47])[CH:43]([CH3:45])[CH3:44])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)C(C)C)(C)C.C(=O)([O-])O.[Na+]>C([O-])(=O)C.C([O-])(=O)C.[Pd+2].C(OCC)(=O)C.C(#N)C>[NH3:9].[C:13]([O:12][C:10]([N:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]/[C:35]1[CH:36]=[CH:37][C:32]([O:31][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:33]([C@@H:39]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH2:40][CH2:41][N:42]([CH:43]([CH3:45])[CH3:44])[CH:46]([CH3:47])[CH3:48])[CH:34]=1)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:11])([CH3:14])([CH3:15])[CH3:16]

参加物

10

反応物 5

HCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 24885301(R)-3-(2-benzyloxy)-5-bromophenyl)-N,N-diisopropyl-3-phenylpropan-1-amineHCID 57933160Di-tert-butyl oct-7-en-1-ylimidodicarbonate

生成物 2

HCID 222AmmoniaHCID 57933221di-tert-butyl[(7E)-8-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}oct-7-en-1-yl]imidodicarbonate

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

di-tert-butyl oct-7-en-1-ylimidodicarbonate (Preparation 48, 649 mg, 1.98 mmol), (3R)-3-[2-(benzyloxy)-5-bromophenyl]-N,N-diisopropyl-3-phenylpropan-1-amine (Prepared according to WO1994/11337, 560 mg, 1.16 mmol), palladium diacetate (27 mg, 0.12 mmol), tris(2-methylphenyl)phosphine (73 mg, 0.24 mmol) and N,N-diisopropylethylamine (0.304 ml, 1.75 mmol) were added to acetonitrile (6 ml) and the mixture was heated to 90° C. and left to stir overnight under nitrogen. Mixture was cooled and saturated aqueous sodium hydrogen carbonate and ethyl acetate were added. Organics separated and washed with saturated aqueous sodium hydrogen carbonate, brine, dried (magnesium sulphate) and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (100/0/0 to 96/4/0.4 by volume) to furnish the title compound as a oil, 530 mg.

後処理

  1. waitleft
  2. temperatureMixture was cooled
  3. customOrganics separated
  4. washwashed with saturated aqueous sodium hydrogen carbonate, brine
  5. dry with materialdried (magnesium sulphate)
  6. customthe solvent removed in vacuo
  7. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

出典と根拠

ORDレコード
ord-6f12f1367def4b99b30b7f65ad290513
出典データセット
uspto-grants-2009_11
特許番号
US07612084B2

反応ノート

読み込み中…