Triethylamine → [trans-1-Benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-yl]methylamine hydrochloride

HRID 1419039

反応式

HRID 1419039 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]C(O)=O)[C:9]1=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:34](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C)C=O>[ClH:19].[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][NH2:34])[C:9]1=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 69946821trans-1-Benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid

生成物 1

HCID 69947635[trans-1-Benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-yl]methylamine hydrochloride

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

In 5 ml of dimethylformamide was dissolved 1.0 g of trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid obtained in Reference Example 5. To the solution was added 0.3 ml of triethylamine, to which was added dropwise, while stirring under ice-cooling, 0.6 g of diphenylphosphoryl azide. The reaction mixture was stirred for one hour at room temperature, which was then poured into ice-water. The mixture was subjected to extraction with ether. The organic layer was washed with water and dried, which was then concentrated under reduced pressure. The concentrate was dissolved in 100 ml of benzene, which was heated for 30 minutes under reflux. The reaction mixture was concentrated under reduced pressure. To the concentrate was added 6 ml of conc. hydrochloric acid, and the mixture was heated for one hour under reflux. The reaction mixture was concentrated under reduced pressure. The concentrate was made alkaline by the addition of a 5% aqueous solution of potassium carbonate, followed by extraction with ethyl acetate. The organic layer was washed with water and dried, then the solvent was distilled off under reduced pressure. To the residue was added an ethanol solution of 4N hydrochloric acid to lead it to hydrochloride to give 0.85 g of [trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-yl]methylamine hydrochloride as crystals, m.p. 245°-250° C.

後処理

  1. customobtained in Reference Example 5
  2. additionto which was added dropwise
  3. temperaturecooling
  4. stirringThe reaction mixture was stirred for one hour at room temperature
  5. extractionThe mixture was subjected to extraction with ether
  6. washThe organic layer was washed with water
  7. customdried
  8. concentrationwhich was then concentrated under reduced pressure
  9. dissolutionThe concentrate was dissolved in 100 ml of benzene
  10. temperaturewhich was heated for 30 minutes
  11. temperatureunder reflux
  12. concentrationThe reaction mixture was concentrated under reduced pressure
  13. additionTo the concentrate was added 6 ml of conc. hydrochloric acid
  14. temperaturethe mixture was heated for one hour
  15. temperatureunder reflux
  16. concentrationThe reaction mixture was concentrated under reduced pressure
  17. additionby the addition of a 5% aqueous solution of potassium carbonate
  18. extractionfollowed by extraction with ethyl acetate
  19. washThe organic layer was washed with water
  20. customdried
  21. distillationthe solvent was distilled off under reduced pressure
  22. additionTo the residue was added an ethanol solution of 4N hydrochloric acid

出典と根拠

ORDレコード
ord-f12f95f577374d72981c61716ef1d3ee
出典データセット
uspto-grants-1999_03
特許番号
US05885979

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