Dicyclohexylcarbodiimide → (R)-quinuclidin-3-yl 2-(6-(benzyloxy)pyridin-3-yl)-2-(phenylamino)acetate

HRID 469490ノート

反応式

HRID 469490 の反応式
[CH2:1]([O:8][C:9]1[N:14]=[CH:13][C:12]([CH:15]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.N1(O)C2C=CC=CC=2N=N1.[N:51]12[CH2:58][CH2:57][CH:54]([CH2:55][CH2:56]1)[C@@H:53](O)[CH2:52]2>C1COCC1>[CH2:1]([O:8][C:9]1[N:14]=[CH:13][C:12]([CH:15]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:16]([O:18][C@@H:53]2[CH:54]3[CH2:57][CH2:58][N:51]([CH2:56][CH2:55]3)[CH2:52]2)=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 585570482-(6-(Benzyloxy)pyridin-3-yl)-2-(phenylamino)acetic acid

生成物 1

HCID 58556981(R)-quinuclidin-3-yl 2-(6-(benzyloxy)pyridin-3-yl)-2-(phenylamino)acetate収率 12%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-(6-(benzyloxy)pyridin-3-yl)-2-(phenylamino)acetic acid (I52) (460 mg, 1.38 mmol) in THF (20 ml), were added DCC (341 mg, 1.65 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (223 mg, 1.65 mmol), and (R)-quinuclidin-3-ol (210 mg, 1.65 mmol). The resulting reaction mixture was stirred at room temperature for 15 hours, and then the solvent was evaporated. DCM is added, the insoluble was filtered off and the organic phase was washed twice with Na2CO3 and brine, dried over Na2SO4 and evaporated. The crude product was purified by flash chromatography (DCM/MeOH=95/5 to 97/3), recovering first diastereomer 1 of C53 (71 mg, 12% yield), then a mixture of diastereomers of C53 (84 mg, 14% yield) and finally diastereomer 2 of C53 (21 mg, 4% yield).

後処理

  1. customThe resulting reaction mixture
  2. customthe solvent was evaporated
  3. additionDCM is added
  4. filtrationthe insoluble was filtered off
  5. washthe organic phase was washed twice with Na2CO3 and brine
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe crude product was purified by flash chromatography (DCM/MeOH=95/5 to 97/3)
  9. customrecovering first diastereomer 1 of C53 (71 mg, 12% yield)
  10. additiona mixture of diastereomers of C53 (84 mg, 14% yield) and finally diastereomer 2 of C53 (21 mg, 4% yield)

出典と根拠

ORDレコード
ord-dc5be6bc7a5840908558e31efd8a95ea
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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