Dicyclohexylcarbodiimide → HCID 58556961、化合物

HRID 77011

反応式

HRID 77011 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[N:20]12[CH2:27][CH2:26][CH:23]([CH2:24][CH2:25]1)[C@@H:22](O)[CH2:21]2.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[N:20]12[CH2:27][CH2:26][CH:23]([CH2:24][CH2:25]1)[C@@H:22]([O:10][C:9](=[O:11])[CH:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[CH2:21]2

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 54890833(4-Fluoro-phenyl)-(3-fluoro-phenylamino)-acetic acid

生成物 1

HCID 58556961HCID 58556961、化合物収率 50%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of (4-fluoro-phenyl)-(3-fluoro-phenylamino)-acetic acid (I83) (510 mg, 1.94 mmol), (R)-quinuclidin-3-ol (246 mg, 1.94 mmol), HOBT (356 mg, 2.32 mmol) and DCC (480 mg, 2.32 mmol) in THF (10 mL) is stirred at RT overnight (UPLC-MS monitoring: complete conversion). The solvent is evaporated, the crude is dissolved in EtOAc and the insoluble is filtered off. The clear solution is washed with 1N K2CO3 and then with brine. The organic layer is dried over Na2SO4, filtered and evaporated. The crude is purified by silica gel chromatography (EtOAc/MeOH=8/2) to give the title compound as a yellow oil (360 mg, 50% yield, mixture of diastereoisomers).

後処理

  1. customThe solvent is evaporated
  2. dissolutionthe crude is dissolved in EtOAc
  3. filtrationthe insoluble is filtered off
  4. washThe clear solution is washed with 1N K2CO3
  5. dry with materialThe organic layer is dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude is purified by silica gel chromatography (EtOAc/MeOH=8/2)

出典と根拠

ORDレコード
ord-8bca5f053377479a86f0ce21ea4d3066
出典データセット
uspto-grants-2014_09
特許番号
US08835682B2

関連ノート

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