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

HRID 469497ノート

反応式

HRID 469497 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-0948b06e0d1748c99a0634691150f52c
出典データセット
uspto-grants-2014_01
特許番号
US08629160B2

反応ノート

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