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Water → Methyl 3-hydroxy-5-(2-oxopyrrolidin-1-yl)benzoate

HRID 852540
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HRID 852540 반응식
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[C:6](N)[CH:5]=1.[N-]=[N+]=[N-].[Na+].[OH2:22]>Cl.CO.CCOCC>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[C:6]([OH:22])[CH:5]=1
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참가 물질

7

반응물 3

HCID 962WaterHCID 33557Sodium AzideHCID 674420033-Amino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester

생성물 1

HCID 22252977Methyl 3-hydroxy-5-(2-oxopyrrolidin-1-yl)benzoate수율 67%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 887Methanol
용매
HCID 3283Diethyl Ether용매

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온도
90 °C

실험 절차

3-Amino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (D4a) (1.50 g, 6.4 mmol, 1 equiv) was dissolved in a mixture of 2N aqueous HCl solution (25 ml) and MeOH (50 ml) at 0° C. and treated portionwise with NaN3 (950 mg, 13.8 mmol, 2.2 equiv) over 20 min. H2O (50 ml) was added and the resulting mixture was heated at 90° C. for 45 min then cooled to room temperature and diluted with Et2O (300 ml). The two layers were separated and the organic phase was dried over MgSO4 and concentrated in vacuo to give 3-hydroxy-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (D37) (1.0 g, 67%) as a tan solid.

후처리

  1. temperaturethen cooled to room temperature
  2. customThe two layers were separated
  3. dry with materialthe organic phase was dried over MgSO4
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-db0c0a5ea7134b99a8b82817089f9646
출처 데이터셋
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07253198B2

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