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benzyl 2-(5-(4'-(2-methyl-5-(trifluoromethyl)oxazole-4-carboxamido)-[1,1'-biphenyl]-4-yl)tetrahydro-2H-pyran-2-yl)acetate → 2-(5-(4'-(2-Methyl-5-(trifluoromethyl)oxazole-4-carboxamido)-[1,1'-biphenyl]-4-yl)tetrahydro-2H-pyran-2-yl)acetic acid

HRID 515392
ノート
印刷プレビュー

反応式

HRID 515392 の反応式
[CH3:1][C:2]1[O:3][C:4]([C:39]([F:42])([F:41])[F:40])=[C:5]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH:22]4[CH2:27][O:26][CH:25]([CH2:28][C:29]([O:31]CC5C=CC=CC=5)=[O:30])[CH2:24][CH2:23]4)=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)=[O:8])[N:6]=1>CCOC(C)=O.[OH-].[OH-].[Pd+2]>[CH3:1][C:2]1[O:3][C:4]([C:39]([F:42])([F:40])[F:41])=[C:5]([C:7]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3[CH:17]=[CH:18][C:19]([CH:22]4[CH2:27][O:26][CH:25]([CH2:28][C:29]([OH:31])=[O:30])[CH2:24][CH2:23]4)=[CH:20][CH:21]=3)=[CH:14][CH:15]=2)=[O:8])[N:6]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 1

HCID 89872728benzyl 2-(5-(4'-(2-methyl-5-(trifluoromethyl)oxazole-4-carboxamido)-[1,1'-biphenyl]-4-yl)tetrahydro-2H-pyran-2-yl)acetate

生成物 1

HCID 721949032-(5-(4'-(2-Methyl-5-(trifluoromethyl)oxazole-4-carboxamido)-[1,1'-biphenyl]-4-yl)tetrahydro-2H-pyran-2-yl)acetic acid収率 80%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 9942167Palladium hydroxide溶媒

実験手順

Benzyl 2-(5-(4′-(2-methyl-5-(trifluoromethyl)oxazole-4-carboxamido)-[1,1′-biphenyl]-4-yl)tetrahydro-2H-pyran-2-yl)acetate was dissolved in EtOAc and hydrogenated with 10% Pd(OH)2/C under H2 balloon for 30 min. The reaction mixture was filtered off to remove the catalyst and the filtrate was concentrated. The residue was purified by reverse HPLC (8 to 50% ACN-water (0.1% NH40H) with X-bridge C8 column) to give the title compound 93 mg (yield 80%) as a mixture of cis/trans isomer (ratio of 1:3). After chiral SFC separation (CL2-20×250 mm, isocratic 45% MeOH in CO2, 75% g/min flow, 220 nM UV) afforded the cis and trans enantiomes:

後処理

  1. filtrationThe reaction mixture was filtered off
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by reverse HPLC (8 to 50% ACN-water (0.1% NH40H) with X-bridge C8 column)

出典と根拠

ORDレコード
ord-bc6010e23e774e0fa86723a811d9d282
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09108956B2

反応ノート

読み込み中…

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