Citiolone → (2S)-2-acetamido-4-sulfanylbutanoic acid

HRID 1259017ノート

反応式

HRID 1259017 の反応式
[OH-:1].[Na+].[CH3:3][C:4]([NH:6][CH:7]1[C:11](=[O:12])[S:10][CH2:9][CH2:8]1)=[O:5]>Cl>[C:4]([NH:6][C@H:7]([C:11]([OH:12])=[O:1])[CH2:8][CH2:9][SH:10])(=[O:5])[CH3:3]

参加物

4

反応物 2

HCID 14520CitioloneHCID 14798Sodium Hydroxide

生成物 1

HCID 165598(2S)-2-acetamido-4-sulfanylbutanoic acid収率 90%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

反応条件

温度
50 °C

実験手順

NaOH (1 M deoxygenated aqueous solution, 100 mL) was dropwise added to DL-N-acetylhomocysteine thiolactone (4.00 g, 25.124 mmol). Addition time: 15 min. The reaction mixture was warmed up to 50° C. and allowed to react for 30 min. The reaction was cooled down to 0° C., acidified with HCl (10% aqueous solution, 30 mL) and the product was extracted with nBuOH (4×70 mL). The organic layer was dried over Na2SO4 (anhydrous), filtered and concentrated. The crude residue was slurred with Et2O/hexanes (1:3, 150 mL) to furnish 4.00 g of DL-N-acetylhomocysteine (white solid, yield: 90%).

後処理

  1. additionAddition time
  2. custom15 min
  3. customto react for 30 min
  4. temperatureThe reaction was cooled down to 0° C.
  5. extractionthe product was extracted with nBuOH (4×70 mL)
  6. dry with materialThe organic layer was dried over Na2SO4 (anhydrous)
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-653b366daac1465b8a8cb078315c6190
出典データセット
uspto-grants-2013_06
特許番号
US08466197B2

反応ノート

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