Dicyclohexylcarbodiimide → ethyl 3-(1-(6-methoxypyridin-3-yl)-2-oxo-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate

HRID 469497노트

반응식

HRID 469497 반응식
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([NH:12][CH:13]([C:17]2[CH:18]=[N:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[C:14]([OH:16])=[O:15])[CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:2].[N:25]12[CH2:32][CH2:31][CH:28]([CH2:29][CH2:30]1)[C@@H:27](O)[CH2:26]2.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[CH3:24][O:23][C:20]1[N:19]=[CH:18][C:17]([CH:13]([NH:12][C:8]2[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=2)[C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:14](=[O:16])[O:15][C@@H:27]2[CH:28]3[CH2:31][CH2:32][N:25]([CH2:30][CH2:29]3)[CH2:26]2)=[CH:22][CH:21]=1

참가 물질

6

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 585569882-(3-(Ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetic acid

생성물 1

HCID 58556990ethyl 3-(1-(6-methoxypyridin-3-yl)-2-oxo-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate수율 31.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetic acid (I64) (951 mg, 2.51 mmol), (R)-quinuclidin-3-ol (694 mg, 5.47 mmol), HOBT (837 mg, 5.47 mmol), and DCC (1.13 g, 5.47 mmol) in dry THF (35 ml) was stirred at room temperature overnight. The solvent was evaporated, and the crude product was partitioned between DCM and 2M K2CO3. The organic phase was dried over Na2SO4, filtered and evaporated to dryness. The crude product was purified by flash chromatography (DMC/MeOH=97/3 to 95/5) to obtain ethyl 3-(1-(6-methoxypyridin-3-yl)-2-oxo-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate (348 mg, 27.5% yield).

후처리

  1. customThe solvent was evaporated
  2. customthe crude product was partitioned between DCM and 2M K2CO3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude product was purified by flash chromatography (DMC/MeOH=97/3 to 95/5)

출처 및 근거

ORD 기록
ord-0948b06e0d1748c99a0634691150f52c
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629160B2

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