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Triethylamine → (2R)-2-amino-N-(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)butanamide

HRID 1505351
ノート
印刷プレビュー

反応式

HRID 1505351 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[N:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[O:16][CH3:17].CC(OC([NH:25][C@H:26]([CH2:30][CH3:31])[C:27](O)=[O:28])=O)(C)C.CCN(CC)CC.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>C(OCC)(=O)C>[NH2:25][C@H:26]([CH2:30][CH3:31])[C:27]([NH:15][C:12]1[CH:13]=[N:14][C:9]([O:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([O:16][CH3:17])[CH:4]=2)=[CH:10][CH:11]=1)=[O:28]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 2755936(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acidHCID 672355973-Amino-6-(3-methoxy-4-methylphenoxy)pyridine2 回

生成物 1

HCID 67236842(2R)-2-amino-N-(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)butanamide収率 119.3%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
0 °C

実験手順

6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinamine (Intermediate 50, 500 g), (2R)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)butanoic acid (530 g) and Et3N (905 mL) are mixed together in ethyl acetate (2 L) and stirred at 0° C. until complete dissolution. ®T3P (2.15 L) was added dropwise in 30 minutes maintaining the temperature at ˜0° C. Ethyl acetate (500 mL) was added for washing the line. Work-up: 10% w/w sodium carbonate aqueous solution (2.5 L) was added and the mixture was stirred for 20 minutes. Then water (1.5 L) and ethyl acetate (1 L) were added and the two phases separated. The organic layer was washed with 10% w/w sodium carbonate aqueous solution (2.5 L), stirring the mixture for 10 minutes before separation of phases, then with 28% malic acid aqueous solution (2.5 L) and finally with 20% NaCl aqueous solution (2.5 L). The organic solution was concentrated to the lowest volume (<2 L), acetonitrile (5 L) was added, the solution was concentrated to the lowest volume (<2 L) and acetonitrile was added up to 12.5 L (it is a solution of Intermediate 64 in acetonitrile). To this solution, 5-6N HCl solution in Isopropanol (2.5 L) was added at 20° C. and the resulting reaction mixture was stirred at 45° C. for 1.5 hours. The obtained suspension was cooled to 20° C., stirred for 1 hour and then filtered. The collected solid was washed with 5/1 acetonitrile/Isopropanol (3×1.5 L), then dried under vacuum at 40° C., until constant weight, obtaining the title compound (817 g).

後処理

  1. temperaturemaintaining the temperature at ˜0° C
  2. washfor washing the line
  3. addition10% w/w sodium carbonate aqueous solution (2.5 L) was added
  4. stirringthe mixture was stirred for 20 minutes
  5. additionThen water (1.5 L) and ethyl acetate (1 L) were added
  6. customthe two phases separated
  7. washThe organic layer was washed with 10% w/w sodium carbonate aqueous solution (2.5 L)
  8. stirringstirring the mixture for 10 minutes
  9. custombefore separation of phases
  10. concentrationThe organic solution was concentrated to the lowest volume (<2 L), acetonitrile (5 L)
  11. additionwas added
  12. concentrationthe solution was concentrated to the lowest volume (<2 L) and acetonitrile
  13. additionwas added up to 12.5 L (it
  14. additionTo this solution, 5-6N HCl solution in Isopropanol (2.5 L) was added at 20° C.
  15. customthe resulting reaction mixture
  16. stirringwas stirred at 45° C. for 1.5 hours
  17. temperatureThe obtained suspension was cooled to 20° C.
  18. stirringstirred for 1 hour
  19. filtrationfiltered
  20. washThe collected solid was washed with 5/1 acetonitrile/Isopropanol (3×1.5 L)
  21. customdried under vacuum at 40° C., until constant weight

出典と根拠

ORDレコード
ord-06d9e2798c054b63aec9eb1e87d5cafd
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09216967B2

反応ノート

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