Acetic Anhydride → N-[trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-ylmethyl]-N-acetyl glycine

HRID 1419041

反応式

HRID 1419041 の反応式
[CH2:1]([N:8]1[C:14]2[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:13]=2[C@@H:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[O:11][C@H:10]([CH2:27][NH:28][CH2:29][C:30]([OH:32])=[O:31])[C:9]1=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:34](OC(=O)C)(=[O:36])[CH3:35].C(N(CC)CC)C>CO>[CH2:1]([N:8]1[C:14]2[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:13]=2[C@@H:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[O:11][C@H:10]([CH2:27][N:28]([C:34](=[O:36])[CH3:35])[CH2:29][C:30]([OH:32])=[O:31])[C:9]1=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 69947765N-[trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-ylmethyl]glycine

生成物 1

HCID 69947325N-[trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-ylmethyl]-N-acetyl glycine

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

In 4 ml of methanol was dissolved 60 mg of ethyl ester of N-[trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-ylmethyl]glycine obtained in Example 40. To the solution were added 0.2 ml of acetic anhydride and 0.2 ml of triethylamine. The mixture was heated for one hour under reflux while stirring. The reaction mixture was concentrated under reduced pressure, which was subjected to extraction with ethyl acetate. The organic layer was washed with an aqueous solution of potassium hydrogensulfate, an aqueous solution of sodium hydrogencarbonate and water, which was then dried, followed by distilling off the solvent. The residue was dissolved in 4 ml of methanol, to which was added 2 ml of a 5% aqueous solution of potassium carbonate. The mixture was stirred for 30 minutes at 60° C. The reaction mixture was concentrated under reduced pressure, to which was added 1N hydrochloric acid to acidify the solution, followed by extraction with ethyl acetate. The organic layer was washed with water and dried, then the solvent was distilled off under reduced pressure. From the residue, 45 mg of N-[trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-ylmethyl]-N-acetyl glycine was obtained as crystals, m.p. 143°-145° C.

後処理

  1. temperatureThe mixture was heated for one hour
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated under reduced pressure, which
  4. extractionwas subjected to extraction with ethyl acetate
  5. washThe organic layer was washed with an aqueous solution of potassium hydrogensulfate
  6. dry with materialan aqueous solution of sodium hydrogencarbonate and water, which was then dried
  7. distillationby distilling off the solvent
  8. dissolutionThe residue was dissolved in 4 ml of methanol, to which
  9. additionwas added 2 ml of a 5% aqueous solution of potassium carbonate
  10. stirringThe mixture was stirred for 30 minutes at 60° C
  11. concentrationThe reaction mixture was concentrated under reduced pressure, to which
  12. additionwas added 1N hydrochloric acid
  13. extractionfollowed by extraction with ethyl acetate
  14. washThe organic layer was washed with water
  15. customdried
  16. distillationthe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-0cac46bb7cac45b088a5ff8dcbdcab50
出典データセット
uspto-grants-1999_03
特許番号
US05885979

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