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

HRID 469490노트

반응식

HRID 469490 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-dc5be6bc7a5840908558e31efd8a95ea
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629160B2

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