Benzoin → HCID 54104002、化合物

HRID 380098

反応式

HRID 380098 の反応式
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@@H:2]1[C:7]([OH:9])=O.[C:10]1([C:16]([CH:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)O)=O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([N:28]=C=NCCCN(C)C)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:10]1([C:16]2[N:28]=[C:7]([C@@H:2]3[NH:1][C:5](=[O:6])[CH2:4][CH2:3]3)[O:9][C:18]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

6

反応物 3

HCID 8400BenzoinHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 439685D-Pyroglutamic acid

生成物 1

HCID 54104002HCID 54104002、化合物

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of D-pyroglutamic acid (30 g) in CH2Cl2 (200 ml) were added benzoin (74 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (68 ml) and 4-dimethylaminopyridine (30 g) at room temperature under N2. After being stirred for 12 hours at room temperature, the solvent was evaporated in vacuo, and the residue was partitioned between ethyl acetate and water. The organic layer was washed with 1N-HCl solution, sat. NaHCO3 and brine, dried over MgSO4, and evaporated in vacuo. The obtained compound and ammonium acetate (60 g) were dissolved in acetic acid (500 ml) and the mixture was stirred for 4 hours at 100° C. After the solvent was removed, the residue was partitioned between ethyl acetate and water. The organic layer was washed with water, sat. NaHCO3 and brine. The dried solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel to give (5R)-5-(4,5-diphenyloxazol-2-yl)pyrrolidin-2-one (21.2 g).

後処理

  1. customthe solvent was evaporated in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with 1N-HCl solution, sat. NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. dissolutionThe obtained compound and ammonium acetate (60 g) were dissolved in acetic acid (500 ml)
  7. stirringthe mixture was stirred for 4 hours at 100° C
  8. customAfter the solvent was removed
  9. customthe residue was partitioned between ethyl acetate and water
  10. washThe organic layer was washed with water, sat. NaHCO3 and brine
  11. customThe dried solvent was evaporated in vacuo
  12. customthe residue was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-4711f1f8d222417aacbc503ba9706a33
出典データセット
uspto-grants-2001_10
特許番号
US06300344B1

関連ノート

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