2,4-Dimethoxybenzyl alcohol → rac-(trans)-Cyclopentane-1,2-dicarboxylic acid mono-(2,4-dimethoxy-benzyl)ester

HRID 547849

反応式

HRID 547849 の反応式
[C@@H:1]1([C:9]([OH:11])=[O:10])[CH2:5][CH2:4][CH2:3][C@H:2]1[C:6]([OH:8])=[O:7].[CH3:12][O:13][C:14]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:15]=1[CH2:16]O.CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.CN(C=O)C.O.C([O-])(O)=O.[Na+]>[CH3:12][O:13][C:14]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:15]=1[CH2:16][O:7][C:6]([C@@H:2]1[CH2:3][CH2:4][CH2:5][C@H:1]1[C:9]([OH:11])=[O:10])=[O:8]

参加物

8

反応物 3

HCID 817502,4-Dimethoxybenzyl alcoholHCID 7273751,2-Cyclopentanedicarboxylic acid, (1R,2R)-rel-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 67153742rac-(trans)-Cyclopentane-1,2-dicarboxylic acid mono-(2,4-dimethoxy-benzyl)ester

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of (trans)-cyclopentane-1,2-dicarboxylic acid (1.90 g, 12 mmol), 2,4-dimethoxy-benzyl alcohol (2.02 g, 12 mmol), DMAP (73 mg, 0.6 mmol) in DMF (30 mL), chilled in an ice bath, was added EDC.HCl (2.53 g, 13.2 mmol) in two portions. The mixture was stirred at ice bath temperature for 15 min and warmed to RT for 4 hrs. The reaction mixture was diluted with H2O (100 mL) and saturated NaHCO3 (40 mL). The aqueous mixture was extracted with EtOAC (3×30 mL), acidified to pH 3 with saturated KHSO4 and extracted with EtOAc (3×30 mL). The combined organic layers were washed with H2O (2×25 mL), saturated NaCl (25 mL), dried over MgSO4, filtered and evaporated. The crude material was re-dissolved in CHCl3 and eluted through a silica gel plug with CHCl3 (100 mL) and then EtOAc (100 mL). The EtOAc fraction was evaporated and pumped to a clear oil, 2.6 g (70%), and used without further purification.

後処理

  1. extractionThe aqueous mixture was extracted with EtOAC (3×30 mL)
  2. extractionextracted with EtOAc (3×30 mL)
  3. washThe combined organic layers were washed with H2O (2×25 mL), saturated NaCl (25 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. dissolutionThe crude material was re-dissolved in CHCl3
  8. washeluted through a silica gel plug with CHCl3 (100 mL)
  9. customThe EtOAc fraction was evaporated
  10. customused without further purification

出典と根拠

ORDレコード
ord-10ad6b1c511a486ba1fc2e1e9aec03bf
出典データセット
uspto-grants-2011_05
特許番号
US07939569B1

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