Tri-o-tolylphosphine → Ammonia

HRID 1433284노트

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HRID 1433284 반응식
[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]

참가 물질

10

반응물 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

생성물 2

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6f12f1367def4b99b30b7f65ad290513
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612084B2

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