Tributylphosphine → ethyl 3-(2-fluoro-4-{({4'-[(4-hydroxytetrahydro-2H-thiopyran-4-yl)methoxy]-2',6'-dimethylbiphenyl-3-yl}methyl) [(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate

HRID 508075ノート

反応式

HRID 508075 の反応式
O[CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[C:14]([CH3:15])=[CH:13][C:12]([O:16][CH2:17][C:18]3([OH:24])[CH2:23][CH2:22][S:21][CH2:20][CH2:19]3)=[CH:11][C:10]=2[CH3:25])[CH:6]=[CH:7][CH:8]=1.[F:26][C:27]1[CH:32]=[C:31]([NH:33][S:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[N+:43]([O-:45])=[O:44])(=[O:36])=[O:35])[CH:30]=[CH:29][C:28]=1[CH2:46][CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[F:26][C:27]1[CH:32]=[C:31]([N:33]([CH2:2][C:3]2[CH:4]=[C:5]([C:9]3[C:14]([CH3:15])=[CH:13][C:12]([O:16][CH2:17][C:18]4([OH:24])[CH2:19][CH2:20][S:21][CH2:22][CH2:23]4)=[CH:11][C:10]=3[CH3:25])[CH:6]=[CH:7][CH:8]=2)[S:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[N+:43]([O-:45])=[O:44])(=[O:35])=[O:36])[CH:30]=[CH:29][C:28]=1[CH2:46][CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49]

参加物

6

反応物 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 231571864-({[3'-(hydroxymethyl)-2,6-dimethylbiphenyl-4-yl]oxy}methyl)tetrahydro-2H-thiopyran-4-olHCID 23157368Ethyl 3-(2-fluoro-4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate

生成物 1

HCID 23157627ethyl 3-(2-fluoro-4-{({4'-[(4-hydroxytetrahydro-2H-thiopyran-4-yl)methoxy]-2',6'-dimethylbiphenyl-3-yl}methyl) [(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate収率 92.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-({[3′-(hydroxymethyl)-2,6-dimethylbiphenyl-4-yl]oxy}methyl)tetrahydro-2H-thiopyran-4-ol (0.90 g, 2.51 mmol), ethyl 3-(2-fluoro-4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate (1.05 g, 2.64 mmol) and tributylphosphine (0.86 mL, 3.26 mmol) in tetrahydrofuran (15 mL) was added 1,1′-(azodicarbonyl)dipiperidine (0.85 g, 3.26 mmol) under stirring at room temperature, and the mixture was stirred for 10 hr. The resulting precipitate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=2/1) to give the title compound (1.71 g, yield 92%) as a pale-yellow amorphous powder.

後処理

  1. stirringthe mixture was stirred for 10 hr
  2. filtrationThe resulting precipitate was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=2/1)

出典と根拠

ORDレコード
ord-2c32ec83a7794e8a962bf80857442f8c
出典データセット
uspto-grants-2010_08
特許番号
US07786165B2

反応ノート

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