Dicyclohexylcarbodiimide → (R)-quinuclidin-3-yl 2-phenyl-2-(o-tolylamino)acetate

HRID 76982

反応式

HRID 76982 の反応式
C1CCC(N=C=NC2CCCCC2)CC1.Cl.[C:17]1([CH:23]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH3:34])[C:24]([OH:26])=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=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>[N:45]12[CH2:52][CH2:51][CH:48]([CH2:49][CH2:50]1)[C@@H:47]([O:25][C:24](=[O:26])[CH:23]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH3:34])[CH2:46]2

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 67124826Phenyl-o-methylphenylamino-acetic acid hydrochloride

生成物 1

HCID 46840573(R)-quinuclidin-3-yl 2-phenyl-2-(o-tolylamino)acetate収率 103%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

PS-DCC (1.15 g, 1.44 mmol, loading: 1.25 mmol/g) is suspended in THF (15 mL). Phenyl-o-methylphenylamino-acetic acid hydrochloride (I38) (200 mg, 0.72 mmol) and HOBT (221 mg, 1.44 mmol) are added, followed by (R)-quinuclidin-3-ol (275 mg, 2.16 mmol) and the mixture is shaken for 16 hours at RT. PS-DCC is filtered off and the filtrate is evaporated. The resulting residue is dissolved in EtOAc and washed sequentially with water, sat. NaHCO3, water and brine. The organic layer is dried over Na2SO4, filtered and evaporated to give the title compound as a colorless oil (260 mg, quantitative yield, mixture of diastereoisomers).

後処理

  1. filtrationPS-DCC is filtered off
  2. customthe filtrate is evaporated
  3. dissolutionThe resulting residue is dissolved in EtOAc
  4. washwashed sequentially with water, sat. NaHCO3, water and brine
  5. dry with materialThe organic layer is dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

出典と根拠

ORDレコード
ord-fa2f4e8b8cfa400a9064e04cb8dbcc6a
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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