(R)-2-(N-benzyl-2-chloroacetamido)-3-hydroxypropanoic acid → (R)-4-Benzyl-5-oxo-3-morpholinecarboxylic Acid

HRID 249887ノート

反応式

HRID 249887 の反応式
[CH2:1]([N:8]([C@H:13]([CH2:17][OH:18])[C:14]([OH:16])=[O:15])[C:9](=[O:12])[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(C)(C)C.[K+]>C(O)(C)(C)C>[CH2:1]([N:8]1[C:9](=[O:12])[CH2:10][O:18][CH2:17][C@@H:13]1[C:14]([OH:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 13543368(R)-2-(N-benzyl-2-chloroacetamido)-3-hydroxypropanoic acidHCID 23665647Potassium tert-butoxide

生成物 1

HCID 13543371(R)-4-Benzyl-5-oxo-3-morpholinecarboxylic Acid収率 59%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

反応条件

温度
110 °C

実験手順

To a solution of (R)-2-(N-benzyl-2-chloroacetamido)-3-hydroxypropanoic acid (1.53 g, 5.63 mmol) in tert-butanol was added potassium tert-butanolate and the reaction mixture heated to 110° C. for three h, then cooled to room temperature and concentrated to dryness. The residue was acidified with 1 N HCl to pH 1 and the aqueous solution extracted with EtOAc (3×250 mL). The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 10 to 30% CH3OH in CH2Cl2 with 1% acetic acid) to provide (R)-4-benzyl-5-oxomorpholine-3-carboxylic acid (780 mg, 59%) as a yellow foam. 1H NMR and MS consistent.

後処理

  1. temperaturecooled to room temperature
  2. concentrationconcentrated to dryness
  3. extractionthe aqueous solution extracted with EtOAc (3×250 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (silica gel, 10 to 30% CH3OH in CH2Cl2 with 1% acetic acid)

出典と根拠

ORDレコード
ord-492b44967f864f49bed5e17b652b7f80
出典データセット
uspto-grants-2011_01
特許番号
US07863271B2

反応ノート

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