Chloroacetyl chloride → (3S)-5-Oxo-4-(phenylmethyl)-3-morpholinecarboxylic acid

HRID 1366556노트

반응식

HRID 1366556 반응식
[CH2:1]([NH:8][C@H:9]([C:12]([OH:14])=[O:13])[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:16][C:17](Cl)=[O:18]>[OH-].[Na+]>[O:18]=[C:17]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@H:9]([C:12]([OH:14])=[O:13])[CH2:10][O:11][CH2:16]1

참가 물질

4

반응물 2

HCID 6577Chloroacetyl chlorideHCID 853606(2S)-2-(benzylamino)-3-hydroxypropanoic acid

생성물 1

HCID 13543372(3S)-5-Oxo-4-(phenylmethyl)-3-morpholinecarboxylic acid수율 19%

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매2회

실험 절차

To a 0° C. solution of N-benzylserine (19.15 g, 105.7 mmol) in 2 N aq. NaOH (100 mL) was added chloroacetyl chloride (10.2 mL, 126.4 mmol) dropwise, and the solution was stirred for 45 min. To the solution was added 30% aq. NaOH (40 mL) dropwise, and the reaction was stirred for 1 h, and then stirred and warmed to room temperature for 72 h. The reaction was adjusted to pH 1 and extracted with three portions of EtOAc. The combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was washed with EtOAc/hexane to give (3S)-5-oxo-4-(phenylmethyl)-3-morpholinecarboxylic acid (4.61 g, 19% yield).

후처리

  1. stirringthe reaction was stirred for 1 h
  2. stirringstirred
  3. extractionextracted with three portions of EtOAc
  4. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washThe residue was washed with EtOAc/hexane

출처 및 근거

ORD 기록
ord-d9d6e383901144a08093e3fc7bb75400
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893056B2

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