Dicyclohexylcarbodiimide → (R)-quinuclidin-3-yl 2-(3-fluorophenyl)-2-(phenylamino)acetate

HRID 1044044ノート

反応式

HRID 1044044 の反応式
C1CCC(N=C=NC2CCCCC2)CC1.Cl.[F:17][C:18]1[CH:19]=[C:20]([CH:24]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:25]([OH:27])=[O:26])[CH:21]=[CH:22][CH:23]=1.C1C=CC2N(O)N=NC=2C=1.[N:45]12[CH2:52][CH2:51][CH:48]([CH2:49][CH2:50]1)[C@@H:47](O)[CH2:46]2>C1COCC1>[F:17][C:18]1[CH:19]=[C:20]([CH:24]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:25]([O:27][C@@H:47]2[CH:48]3[CH2:51][CH2:52][N:45]([CH2:50][CH2:49]3)[CH2:46]2)=[O:26])[CH:21]=[CH:22][CH:23]=1

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 67124831HCID 67124831、化合物

生成物 1

HCID 58556978(R)-quinuclidin-3-yl 2-(3-fluorophenyl)-2-(phenylamino)acetate収率 56%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

PS-DCC (982 mg, 1.31 mmol, loading: 1.33 mmol/g) was suspended in dry THF (15 ml). 2-(3-Fluorophenyl)-2-(phenylamino)acetic acid hydrochloride (I17) (184 mg, 0.65 mmol), HOBT (200 mg, 1.31 mmol), and (R)-quinuclidin-3-ol (249 mg, 1.96 mmol) were added, and the mixture was shaken at room temperature overnight. PS-DCC was removed by filtration, and the filtrate is evaporated. The residue was dissolved in EtOAc and washed with NaHCO3, water and brine. The organic layer was dried over Na2SO4, filtered, and evaporated to dryness. The crude compound was purified by filtration through a pad of silica-gel using DCM/MeOH=9/1 as the eluent. The title compound was obtained (129 mg, 56% yield, mixture of diastereomers).

後処理

  1. customPS-DCC was removed by filtration
  2. customthe filtrate is evaporated
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with NaHCO3, water and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. filtrationThe crude compound was purified by filtration through a pad of silica-gel

出典と根拠

ORDレコード
ord-143b2466e3c645319cfab185e67cf7e2
出典データセット
uspto-grants-2013_10
特許番号
US08563577B2

反応ノート

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