Dicyclohexylcarbodiimide → (R)-quinuclidin-3-yl 2-(methyl(phenyl)amino)-2-phenylacetate

HRID 1044056노트

반응식

HRID 1044056 반응식
[CH3:1][N:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4]([OH:6])=[O:5].[N:19]12[CH2:26][CH2:25][CH:22]([CH2:23][CH2:24]1)[C@@H:21](O)[CH2:20]2.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[CH3:1][N:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4]([O:6][C@@H:21]1[CH:22]2[CH2:25][CH2:26][N:19]([CH2:24][CH2:23]2)[CH2:20]1)=[O:5]

참가 물질

6

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 20993142HCID 20993142, 화합물

생성물 1

HCID 46840263(R)-quinuclidin-3-yl 2-(methyl(phenyl)amino)-2-phenylacetate수율 68.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2-(Methyl(phenyl)amino)-2-phenylacetic acid (I35) (2.20 g, 9.12 mmol) was dissolved in THF (25 ml), and (R)-quinuclidin-3-ol (1.28 g, 10.0 mmol) was added. To the resulting solution, HOBt (1.23 g, 9.12 mmol) and DCC (1.88 g, 9.12 mmol) were added, and the mixture was stirred at room temperature for three days. THF was removed under vacuum and the residue was portioned between H2O and EtOAc. The organic phase was washed with a saturated aqueous Na2CO3 solution, dried over Na2SO4 and evaporated to dryness. The crude was purified by flash chromatography (EtOAc to EtOAc/MeOH=75/25) to afford (R)-quinuclidin-3-yl 2-(methyl(phenyl)amino)-2-phenylacetate (2.2 g, 68.8% yield, mixture of diastereomers).

후처리

  1. customTHF was removed under vacuum
  2. washThe organic phase was washed with a saturated aqueous Na2CO3 solution
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness
  5. customThe crude was purified by flash chromatography (EtOAc to EtOAc/MeOH=75/25)

출처 및 근거

ORD 기록
ord-9edc687e1eef40afb6d47e5bbab87efb
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563577B2

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