Acetic Acid → 3-Amino-4-{(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-methylpiperidin-1-yl}-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate

HRID 1499518노트

반응식

HRID 1499518 반응식
[C:1]([O:4][CH:5]1[C:9]2=[N:10][CH:11]=[C:12]([N+:29]([O-])=O)[C:13]([N:14]3[CH2:19][C@H:18]([CH3:20])[CH2:17][C@H:16]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:15]3)=[C:8]2[CH2:7][CH2:6]1)(=[O:3])[CH3:2].CC(O)=O>CCOC(C)=O.[Fe]>[C:1]([O:4][CH:5]1[C:9]2=[N:10][CH:11]=[C:12]([NH2:29])[C:13]([N:14]3[CH2:19][C@H:18]([CH3:20])[CH2:17][C@H:16]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:15]3)=[C:8]2[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

참가 물질

5

반응물 2

HCID 176Acetic AcidHCID 867267494-{(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-methylpiperidin-1-yl}-3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate

생성물 1

HCID 867267483-Amino-4-{(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-methylpiperidin-1-yl}-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate수율 96%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 4-{(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-methylpiperidin-1-yl}-3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate (11.2 mg, 0.026 mmol), AcOH (73.3 μL) and iron powder (14.4 mg, 0.26 mmol) was stirred at room temperature for 3 h. The reaction mixture was diluted with EtOAc, filtered and washed with more EtOAc. The filtrate was concentrated under vacuum, and the residue was diluted with EtOAc and neutralized with Na2CO3 solution. The mixture was stirred at room temperature for 30 min. The organic layer was separated, dried over Na2SO4, filtered and concentrated under vacuum to give the sub-title compound as a yellowish solid (10.0 mg, 96%). LCMS calc. for C21H33N4O4 (M+H)+: m/z=405.2. Found: 405.1.

후처리

  1. filtrationfiltered
  2. washwashed with more EtOAc
  3. concentrationThe filtrate was concentrated under vacuum
  4. additionthe residue was diluted with EtOAc and neutralized with Na2CO3 solution
  5. stirringThe mixture was stirred at room temperature for 30 min
  6. customThe organic layer was separated
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-6c13ac9ae24949e8bfb7f7e36a28b025
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09200004B2

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