Hydrochloric Acid → (2E)-3-(5-{[(3R)-1-(benzyloxy)-6-oxo-3-piperidinyl]amino}-2-pyrazinyl)-N-hydroxyacrylamide

HRID 226489노트

반응식

HRID 226489 반응식
[CH2:1]([O:8][N:9]1[C:14](=[O:15])[CH2:13][CH2:12][C@@H:11]([NH:16][C:17]2[N:18]=[CH:19][C:20](/[CH:23]=[CH:24]/[C:25](OCC)=[O:26])=[N:21][CH:22]=2)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:31][OH:32].C[O-].[Na+].Cl>CO>[CH2:1]([O:8][N:9]1[C:14](=[O:15])[CH2:13][CH2:12][C@@H:11]([NH:16][C:17]2[N:18]=[CH:19][C:20](/[CH:23]=[CH:24]/[C:25]([NH:31][OH:32])=[O:26])=[N:21][CH:22]=2)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 86603704ethyl (2E)-3-(5-{[(3R)-1-(benzyloxy)-6-oxo-3-piperidinyl]amino}-2-pyrazinyl)acrylate

생성물 1

HCID 136335111(2E)-3-(5-{[(3R)-1-(benzyloxy)-6-oxo-3-piperidinyl]amino}-2-pyrazinyl)-N-hydroxyacrylamide수율 8%

시약·촉매·용매 1

HCID 887Methanol용매2회

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온도
0 °C

실험 절차

To a solution of ethyl (2E)-3-(5-{[(3R)-1-(benzyloxy)-6-oxo-3-piperidinyl]amino}-2-pyrazinyl)acrylate (200 mg, 0.50 mmol) in methanol (5 mL) was added hydroxylamine hydrochloride (175 mg, 2.52 mmol) at ambient temperature under nitrogen. After cooling, 1M sodium methanolate in methanol (5 mL) was added dropwise to the mixture over 1 h, the reaction mixture was stirred at 0° C. for 2 hrs and at ambient temperature for 4 hrs. The reaction mixture was adjusted to PH 6.0 with 1 mol/L hydrochloric acid and evaporated in vacuo. The residue was dissolved in ethanol and the precipitate was removed by filtration. The solvent was evaporated in vacuo. The residue was purified by preparative HPLC (CH3CN, 20% NH4HCO3/30%˜90%, gradient) to give (2E)-3-(5-{[(3R)-1-(benzyloxy)-6-oxo-3-piperidinyl]amino}-2-pyrazinyl)-N-hydroxyacrylamide (15 mg, 8%) as a powder.

후처리

  1. temperatureAfter cooling
  2. customevaporated in vacuo
  3. dissolutionThe residue was dissolved in ethanol
  4. customthe precipitate was removed by filtration
  5. customThe solvent was evaporated in vacuo
  6. customThe residue was purified by preparative HPLC (CH3CN, 20% NH4HCO3/30%˜90%, gradient)

출처 및 근거

ORD 기록
ord-37621c1011f44d348b0b5e84b9b9b94f
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557127B2

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