D-Pyroglutamic acid → (R)-N-((1-(5-oxopyrrolidine-2-carbonyl)piperidin-4-yl)methyl)-3,5-bis(trifluoromethyl)benzamide

HRID 508635

反応式

HRID 508635 の反応式
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:24])[C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=2)[CH2:3][CH2:2]1.[O:25]=[C:26]1[NH:30][C@@H:29]([C:31](O)=[O:32])[CH2:28][CH2:27]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O>[O:25]=[C:26]1[NH:30][C@@H:29]([C:31]([N:1]2[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:24])[C:10]3[CH:11]=[C:12]([C:20]([F:21])([F:22])[F:23])[CH:13]=[C:14]([C:16]([F:18])([F:19])[F:17])[CH:15]=3)[CH2:3][CH2:2]2)=[O:32])[CH2:28][CH2:27]1

参加物

7

反応物 4

HCID 439685D-Pyroglutamic acidHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57993323N-(piperidin-4-ylmethyl)-3,5-bis(trifluoromethyl)benzamide

生成物 1

HCID 57993336(R)-N-((1-(5-oxopyrrolidine-2-carbonyl)piperidin-4-yl)methyl)-3,5-bis(trifluoromethyl)benzamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
-20 °C

実験手順

A solution of N-(piperidin-4-ylmethyl)-3,5-bis(trifluoromethyl)benzamide (48 mg, 0.14 mmol), TEA (95 μL, 0.68 mmol), and (R)-5-oxopyrrolidine-2-carboxylic acid (20.66 mg, 0.16 mmol) in DMF (1.5 mL) was treated with a solution of HATU (77 mg, 0.20 mmol) in DMF (1 mL). The reaction mixture was stirred overnight then transferred to a test tube containing saturated aqueous NaHCO3 (4 mL) and EtOAc (4 mL). The biphasic mixture was mixed vigorously and allowed to separate for 15 min. After separation, the mixture was cooled to −20° C. until the aqueous layer was frozen. The organic layer was then poured off and the solvent was removed in vacuo at 50° C. The resulting residue was dissolved in CH2Cl2 (1 mL) and treated with 2M HCl in Et2O (3 mL) and allowed to stir overnight at room temperature. The solvent was removed under reduced pressure and the crude solid was purified by HiTOPs.

後処理

  1. customthen transferred to a test tube
  2. additionThe biphasic mixture was mixed vigorously
  3. customto separate for 15 min
  4. customAfter separation
  5. temperaturewas frozen
  6. additionThe organic layer was then poured off
  7. customthe solvent was removed in vacuo at 50° C
  8. dissolutionThe resulting residue was dissolved in CH2Cl2 (1 mL)
  9. additiontreated with 2M HCl in Et2O (3 mL)
  10. stirringto stir overnight at room temperature
  11. customThe solvent was removed under reduced pressure
  12. customthe crude solid was purified by HiTOPs

出典と根拠

ORDレコード
ord-c0bf54677e164a3a9873009a2342a3bd
出典データセット
uspto-grants-2015_08
特許番号
US09096522B2

関連ノート

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