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

HRID 45586ノート

反応式

HRID 45586 の反応式
[CH2:1]([NH:8][C@@H:9]([CH2:13][OH:14])[C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:22][C:23](Cl)=[O:24].[OH-].[Na+]>O1CCCC1.C(OCC)C>[CH2:1]([N:8]1[C:23](=[O:24])[CH2:22][O:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 853606(2S)-2-(benzylamino)-3-hydroxypropanoic acid

生成物 1

HCID 13543372(3S)-5-Oxo-4-(phenylmethyl)-3-morpholinecarboxylic acid収率 60%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (S)-2-(benzylamino)-3-hydroxypropanoic acid (40.0 g, 205 mmol) in tetrahydrofuran (600 mL) was added aqueous potassium carbonate solution (85.0 g, 600 mL) at 0° C. under nitrogen atmosphere, and additionally, chloroacetylchloride (29.0 mL, 369 mmol) was added. After stirring for 2 hours at room temperature, to the mixture was added 30% aqueous sodium hydroxide solution to adjust to pH 13. To the mixture was added diethyl ether, and the organic layer was separated, and then concentrated hydrochloric acid was added to adjust to pH 1, and cooled to 0° C. The precipitated crystal was collected by filtration to give the title compound (29.0 g, 123 mmol, 60%).

後処理

  1. customthe organic layer was separated
  2. additionconcentrated hydrochloric acid was added
  3. temperaturecooled to 0° C
  4. filtrationThe precipitated crystal was collected by filtration

出典と根拠

ORDレコード
ord-07d8faf7d6a948c1a8421e53d31523de
出典データセット
uspto-grants-2013_09
特許番号
US08541585B2

反応ノート

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