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

HRID 924405
ノート
印刷プレビュー

反応式

HRID 924405 の反応式
[C:1]([O:4][CH:5]1[C:9]2=[N:10][CH:11]=[C:12]([N+:28]([O-])=O)[C:13]([N:14]3[CH2:19][CH2:18][CH2:17][C@H:16]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:15]3)=[C:8]2[CH2:7][CH2:6]1)(=[O:3])[CH3:2].CC(O)=O.O>CCOC(C)=O.[Fe]>[C:1]([O:4][CH:5]1[C:9]2=[N:10][CH:11]=[C:12]([NH2:28])[C:13]([N:14]3[CH2:19][CH2:18][CH2:17][C@H:16]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:15]3)=[C:8]2[CH2:7][CH2:6]1)(=[O:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 176Acetic AcidHCID 962WaterHCID 867266934-{(3S)-3-[(tert-Butoxycarbonyl)amino]piperidin-1-yl}-3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate

生成物 1

HCID 867266943-Amino-4-{(3S)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate

試薬・触媒・溶媒 2

HCID 23925Iron触媒
HCID 8857
Ethyl Acetate
溶媒

実験手順

A mixture of 4-{(3S)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate (64.0 mg, 0.152 mmol), AcOH (0.90 mL), water (0.10 mL) and iron powder (149 mg, 2.66 mmol) was stirred at room temperature for 20 min. The mixture was diluted with EtOAc, and filtered through a short silica gel plug. The filtrate was concentrated under reduced pressure, diluted with EtOAc and washed with aq. Na2CO3. The combined organic extract was dried, filtered and concentrated under reduced pressure to give the sub-title compound as a yellow solid. LCMS calc. for C20H31N4O4 (M+H)+: m/z=391.2. Found: 391.1.

後処理

  1. filtrationfiltered through a short silica gel plug
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. additiondiluted with EtOAc
  4. washwashed with aq. Na2CO3
  5. extractionThe combined organic extract
  6. customwas dried
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-99f5ca40f9664b89a619e8e68cc629f4
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09278950B2

反応ノート

読み込み中…

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