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

HRID 249887노트

반응식

HRID 249887 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6386tert-Butanol용매

반응 조건

온도
110 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-492b44967f864f49bed5e17b652b7f80
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863271B2

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