Bromine → 2-(S)-(2-Acetoxymethyl-4-amino-5-bromo-3-methyl-benzyl)-succinic acid diethyl ester

HRID 132360ノート

反応式

HRID 132360 の反応式
[CH2:1]([O:3][C:4](=[O:26])[C@@H:5]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([CH3:20])[C:14]=1[CH2:21][O:22][C:23](=[O:25])[CH3:24])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2].C([O-])(=O)C.[Na+].[Br:32]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:26])[C@@H:5]([CH2:12][C:13]1[CH:18]=[C:17]([Br:32])[C:16]([NH2:19])=[C:15]([CH3:20])[C:14]=1[CH2:21][O:22][C:23](=[O:25])[CH3:24])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2]

参加物

6

反応物 4

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 517045Sodium AcetateHCID 597319272-(S)-(2-Acetoxymethyl-4-amino-3-methyl-benzyl)-succinic acid diethyl ester

生成物 1

HCID 597318802-(S)-(2-Acetoxymethyl-4-amino-5-bromo-3-methyl-benzyl)-succinic acid diethyl ester収率 77%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

2-(S)-(2-Acetoxymethyl-4-amino-3-methyl-benzyl)-succinic acid diethyl ester (7.6 g, 21 mmol) was dissolved in acetic acid (100 mL). Sodium acetate (4.2 g, 51 mmol) was added to the solution. Reaction vessel was placed in a cool water bath to control reaction exotherm. Bromine (1.1 mL, 22 mmol) was added to the mixture in one portion. Reaction stirred at ambient temperature for 10 minutes. Mixture was poured into 1N aqueous sodium thiosulfate solution (400 mL). Material was extracted twice with ethyl acetate. Organic phase was washed successively with water and brine. Organic was dried (magnesium sulfate), filtered and concentrated in vacuo. Silica gel chromatography (ethyl acetate-hexanes) afforded the desired product in 77% yield as an amber oil. MS m/e (M−H)−=440.0, 442.0.

後処理

  1. customReaction vessel
  2. customwas placed in a cool water bath
  3. customreaction exotherm
  4. customReaction
  5. extractionMaterial was extracted twice with ethyl acetate
  6. washOrganic phase was washed successively with water and brine
  7. dry with materialOrganic was dried (magnesium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-5c932ac834464eacbf0e2e32af48138c
出典データセット
uspto-grants-2008_06
特許番号
US07384931B2

反応ノート

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