Dicyclohexylcarbodiimide → HCID 59401120、化合物

HRID 77027ノート

反応式

HRID 77027 の反応式
C1CCC(N=C=NC2CCCCC2)CC1.Cl.[C:17]1([NH:23][CH:24]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=2)[C:25]([OH:27])=[O:26])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1C=CC2N(O)N=NC=2C=1.[N:48]12[CH2:55][CH2:54][CH:51]([CH2:52][CH2:53]1)[C@@H:50](O)[CH2:49]2>C1COCC1>[N:48]12[CH2:55][CH2:54][CH:51]([CH2:52][CH2:53]1)[C@@H:50]([O:26][C:25](=[O:27])[CH:24]([NH:23][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:28]1[CH:33]=[CH:32][C:31]([C:34]([F:35])([F:36])[F:37])=[CH:30][CH:29]=1)[CH2:49]2

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 67425422Phenylamino-(4-trifluoromethyl-phenyl)-acetic acid hydrochloride

生成物 1

HCID 59401120HCID 59401120、化合物収率 45%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

PS-DCC (907 mg, 1.21 mmol, loading: 1.33 mmol/g) is suspended in dry THF (10 mL). Phenylamino-(4-trifluoromethyl-phenyl)-acetic acid hydrochloride (I104) (200 mg, 0.60 mmol), HOBT (185 mg, 1.21 mmol), and (R)-quinuclidin-3-ol (230 mg, 1.81 mmol) are added and the mixture is shaken at RT overnight. PS-DCC is filtered off, the filtrate is evaporated and the residue is dissolved in EtOAc and washed with NaHCO3, water and brine. The organic layer is dried over Na2SO4, filtered and evaporated to dryness. The resulting crude compound is purified by filtration through a pad of silica-gel using DCM/MeOH=9/1 as the eluent. The title compound is obtained as a colorless oil (110 mg, 45% yield, mixture of diastereoisomers).

後処理

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

出典と根拠

ORDレコード
ord-cbe8ae05739d4707bde000cc720c650b
出典データセット
uspto-grants-2014_09
特許番号
US08835682B2

反応ノート

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