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Sodium Carbonate → 1-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine

HRID 343523
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HRID 343523 반응식
C([C@](C(O)=O)(O)[C@](C(=O)C1C=CC(OC)=CC=1)(O)C(O)=O)(=O)C1C=CC(OC)=CC=1.[C:31]1([C:37]2([CH2:42][CH2:43][OH:44])[CH2:41][CH2:40][NH:39][CH2:38]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:51][O:52][C:53]1[CH:61]=[CH:60][C:59]([N:62]2[CH:66]=[N:65][N:64]=[N:63]2)=[CH:58][C:54]=1[C:55](Cl)=[O:56]>C(OCC)(=O)C.O>[CH3:51][O:52][C:53]1[CH:61]=[CH:60][C:59]([N:62]2[CH:66]=[N:65][N:64]=[N:63]2)=[CH:58][C:54]=1[C:55]([N:39]1[CH2:40][CH2:41][C:37]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)([CH2:42][CH2:43][OH:44])[CH2:38]1)=[O:56]
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반응물 3

HCID 10340Sodium CarbonateHCID 153920222-Methoxy-5-(1H-tetrazol-1-yl)benzoyl ChlorideHCID 70109704(-)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid

생성물 1

HCID 184644561-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine

시약·촉매·용매 2

HCID 962Water용매
HCID 8857
Ethyl Acetate
용매
2회

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온도
0 °C

실험 절차

Combine (-)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid salt (56.0 g, 92.1 mmol), sodium carbonate (19.5 g, 184 mmol) in ethyl acetate (2 L) and water (2 L). Cool to about 0° C. in an ice bath. After 30 minutes, slowly add portionwise 2-methoxy-5-(1H-tetrazol-1-yl)benzoyl chloride (92.1 mmol). After the addition is complete, warm to ambient temperature. After 1 hour, dilute the reaction mixture ethyl acetate and extract with water, 1M aqueous hydrochloric acid solution, and then brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give the title compound. Rf =0.48 (9/1 dichloromethane/methanol).

후처리

  1. additionAfter the addition
  2. temperaturewarm to ambient temperature
  3. waitAfter 1 hour
  4. extractionextract with water, 1M aqueous hydrochloric acid solution
  5. dry with materialDry the organic layer over Na2SO4
  6. filtrationfilter
  7. customevaporate in vacuo

출처 및 근거

ORD 기록
ord-beda92ec88e7426397aaf12b2aa85ce9
출처 데이터셋
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05861417

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