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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Water → 2-(6-{(Naphthalene-2-sulfonyl)-[2-(2-oxopyrrolidin-1-yl)ethyl]amino}-3-azabicyclo[3.1.0]hex-3-yl)pyrimidine-5-carboxylic acid

HRID 2079790
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HRID 2079790 반응식
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([N:14]([CH2:32][CH2:33][N:34]1[CH2:38][CH2:37][CH2:36][C:35]1=[O:39])[CH:15]1[CH:20]2[CH:16]1[CH2:17][N:18]([C:21]1[N:26]=[CH:25][C:24]([C:27]([O:29]CC)=[O:28])=[CH:23][N:22]=1)[CH2:19]2)(=[O:13])=[O:12].[O-]CC.[Na+].Cl.NO.O>CCO>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([N:14]([CH2:32][CH2:33][N:34]1[CH2:38][CH2:37][CH2:36][C:35]1=[O:39])[CH:15]1[CH:20]2[CH:16]1[CH2:17][N:18]([C:21]1[N:26]=[CH:25][C:24]([C:27]([OH:29])=[O:28])=[CH:23][N:22]=1)[CH2:19]2)(=[O:12])=[O:13]
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참가 물질

6

반응물 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 2723922Sodium ethoxideHCID 59367586Ethyl 2-(6-{(naphthalene-2-sulfonyl)-[2-(2-oxopyrrolidin-1-yl)ethyl]amino}-3-azabicyclo[3.1.0]hex-3-yl)pyrimidine-5-carboxylate

생성물 1

HCID 593676352-(6-{(Naphthalene-2-sulfonyl)-[2-(2-oxopyrrolidin-1-yl)ethyl]amino}-3-azabicyclo[3.1.0]hex-3-yl)pyrimidine-5-carboxylic acid
수율 32%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
40 °C

실험 절차

To a solution of ethyl 2-(6-{(naphthalene-2-sulfonyl)-[2-(2-oxopyrrolidin-1-yl)ethyl]amino}-3-azabicyclo[3.1.0]hex-3-yl)pyrimidine-5-carboxylate (0.749 g, 1.4 mmol) in EtOH (8 ml) was added sodium ethoxide (1.08 g, 15.8 mmol) and hydroxylamine hydrochloride (1.30 g, 18.7 mmol). The mixture was stirred at 40° C. for 18 h, then water (20 ml) was added. The product was extracted with DCM (2×100 ml), and the combined organic extracts were dried (MgSO4) and concentrated in vacuo. The expected hydroxamate product was in fact proved not to have formed. The reaction yielded instead the acid. Purification by reverse phase HPLC yielded the title compound (232 mg, 32%). This was used directly in the next step without characterisation.

후처리

  1. extractionThe product was extracted with DCM (2×100 ml)
  2. dry with materialthe combined organic extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customto have formed
  5. customThe reaction yielded instead the acid
  6. customPurification by reverse phase HPLC

출처 및 근거

ORD 기록
ord-4c5f0e421843415b8249f550bea273fc
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07932246B2

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