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

HRID 323357
ノート
印刷プレビュー

反応式

HRID 323357 の反応式
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+].[CH3:50][O:51][C:52]1[CH:60]=[CH:59][C:58]([N:61]2[CH:65]=[N:64][N:63]=[N:62]2)=[CH:57][C:53]=1[C:54](Cl)=[O:55].C(OCC)(=O)C>CC(C)=O.O.CC(C)=O.CO.C(OCC)(=O)C>[CH3:50][O:51][C:52]1[CH:60]=[CH:59][C:58]([N:61]2[CH:65]=[N:64][N:63]=[N:62]2)=[CH:57][C:53]=1[C:54]([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:55]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 153920222-Methoxy-5-(1H-tetrazol-1-yl)benzoyl ChlorideHCID 70109704(-)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid

生成物 1

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

試薬・触媒・溶媒 3

HCID 180Acetone溶媒
HCID 18366337Propan-2-one--water (1/1)溶媒
HCID 21584119Ethylacetate methanol溶媒2 回

実験手順

Add (−)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid salt (6.72 g, 11.0 mmol) and sodium bicarbonate (4.87 g, 58 mmol) in acetone/water (50 mL/50 mL). Cool in an ice bath. Add a solution of 2-methoxy-5-(1H-tetrazol-1-yl)benzoyl chloride (1.66 g, 9.9 mmol) in acetone (100 mL). After 30 minutes, warm to ambient temperature. After 60 hours, filter the reaction mixture and dilute the filtrate with ethyl acetate. Extract the filtrate with a saturated aqueous sodium bicarbonate solution and then brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give residue. Chromatograph the residue on silica gel eluting sequentially with ethyl acetate, 3% methanol/ethyl acetate, and then 5% methanol/ethyl acetate to give the title compound: Rf=0.48 (5% methanol/dichloromethane).

後処理

  1. temperatureCool in an ice bath
  2. waitAfter 60 hours
  3. filtrationfilter the reaction mixture
  4. additiondilute the filtrate with ethyl acetate
  5. extractionExtract the filtrate with a saturated aqueous sodium bicarbonate solution
  6. dry with materialDry the organic layer over MgSO4
  7. filtrationfilter
  8. customevaporate in vacuo
  9. customto give residue

出典と根拠

ORDレコード
ord-7ad8846c5c8e4e0eac0ad3034374efbc
出典データセット
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06211199B1

反応ノート

読み込み中…

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