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Citric Acid → (3S,4R)-1-(tert-butoxycarbonyl)-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylic acid

HRID 1260940
ノート
印刷プレビュー

反応式

HRID 1260940 の反応式
C([C@@H]1COC(=O)N1[C:14]([C@H:16]1[C@H:20]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=2)[CH2:19][N:18]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:17]1)=[O:15])C1C=CC=CC=1.[OH-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:41]>C1COCC1>[C:32]([O:31][C:29]([N:18]1[CH2:19][C@@H:20]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=2)[C@H:16]([C:14]([OH:41])=[O:15])[CH2:17]1)=[O:30])([CH3:33])([CH3:34])[CH3:35]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 67231603tert-butyl (3S,4R)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-4-(3,4-dichlorophenyl)pyrrolidine-1-carboxylate

生成物 1

HCID 51441165(3S,4R)-1-(tert-butoxycarbonyl)-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylic acid収率 81%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

To a solution of the compound (2.5 g) obtained in step 3 in THF (27 mL) was added 4N aqueous lithium hydroxide solution (3.6 mL) at room temperature, and the mixture was stirred for 60 hr. The reaction mixture was made slightly acidic with aqueous citric acid solution, and the resultant product was extracted with ethyl acetate. The organic layer was washed with water and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent; 0→70% ethyl acetate/hexane) to give (3S,4R)-1-(tert-butoxycarbonyl)-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylic acid (1.41 g, 81%) as a white powder.

後処理

  1. extractionthe resultant product was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent; 0→70% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-e53fc3c4745b47dcaaa2b46491980895
出典データセット
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08470816B2

反応ノート

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