Dicyclohexylcarbodiimide → HCID 59401140、化合物

HRID 1255083ノート

反応式

HRID 1255083 の反応式
C1CCC(N=C=NC2CCCCC2)CC1.O.N1(O)C2C=CC=CC=2N=N1.Cl.[F:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[NH:35][CH:36]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:37]([OH:39])=[O:38].[N:46]12[CH2:53][CH2:52][CH:49]([CH2:50][CH2:51]1)[C@@H:48](O)[CH2:47]2>C1COCC1>[N:46]12[CH2:53][CH2:52][CH:49]([CH2:50][CH2:51]1)[C@@H:48]([O:38][C:37](=[O:39])[CH:36]([NH:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[F:28])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:47]2

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 914043-Quinuclidinol, (-)-HCID 27960291-Hydroxybenzotriazole hydrateHCID 67425879(2-Fluoro-phenylamino)-phenyl-acetic acid hydrochloride

生成物 1

HCID 59401140HCID 59401140、化合物収率 16.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of DCC (534 mg, 0.71 mmol), 1H-benzo[d][1,2,3]triazol-1-ol hydrate (217 mg, 1:42 mmol), (2-fluoro-phenylamino)-phenyl-acetic acid hydrochloride (I247) (200 mg, 0.71 mmol) and (R)-quinuclidin-3-ol (271 mg, 2.13 mmol) in THF (10 mL) is stirred at RT for 2 days. The solvent is evaporated and the residue is taken up with EtOAc, washed with sat NaHCO3, water and brine. The organic layer is collected, dried over Na2SO4, filtered and evaporated to dryness. The residue is purified by preparative HPLC. The organic solvent is evaporated and the acid aqueous phase is basified with Na2CO3 and extracted with EtOAc. The organic layer is dried (Na2SO4), filtered and evaporated to afford the title compound as yellow oil (41 mg, 16% yield).

後処理

  1. customThe solvent is evaporated
  2. washwashed
  3. customThe organic layer is collected
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue is purified by preparative HPLC
  8. customThe organic solvent is evaporated
  9. extractionextracted with EtOAc
  10. dry with materialThe organic layer is dried (Na2SO4)
  11. filtrationfiltered
  12. customevaporated

出典と根拠

ORDレコード
ord-69b051244da241bfb87ec8c34dab03a4
出典データセット
uspto-grants-2013_06
特許番号
US08455646B2

反応ノート

読み込み中…