Ammonium formate → methyl 4'-[2-[[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]-amino]ethyl]-1,1'-biphenyl-4-carboxylate

HRID 1823128노트

반응식

HRID 1823128 반응식
C([N:8]([CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([O:35][CH3:36])=[O:34])=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)[CH2:9][C@@H:10]([C:12]1[CH:13]=[N:14][C:15](Cl)=[CH:16][CH:17]=1)[OH:11])C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO.O>[OH:11][C@H:10]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[CH2:9][NH:8][CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([O:35][CH3:36])=[O:34])=[CH:29][CH:28]=2)=[CH:25][CH:26]=1

참가 물질

6

반응물 2

HCID 2723923Ammonium formateHCID 86590696methyl 4'-[2-[N-benzyl-N-[(2R)-2-(6-chloro-3-pyridyl)-2-hydroxyethyl]amino]ethyl]-1,1'-biphenyl-4-carboxylate

생성물 1

HCID 69051982methyl 4'-[2-[[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]-amino]ethyl]-1,1'-biphenyl-4-carboxylate수율 92.3%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 962Water용매

실험 절차

Methyl 4′-[2-[N-benzyl-N-[(2R)-2-(6-chloro-3-pyridyl)-2-hydroxyethyl]amino]ethyl]-1,1′-biphenyl-4-carboxylate (470 mg), ammonium formate (296 mg) and palladium on carbon powder (100 mg) in methanol (10 ml) and water (1.0 ml) was refluxed for 30 minutes. The reaction mixture was filtrated and poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. A mixture of the residue was chromatographed (chloroform-methanol) over silica gel to give methyl 4′-[2-[[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]-amino]ethyl]-1,1′-biphenyl-4-carboxylate (326 mg) as a colorless foam.

후처리

  1. filtrationThe reaction mixture was filtrated
  2. additionpoured into water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. additionA mixture of the residue
  8. customwas chromatographed (chloroform-methanol) over silica gel

출처 및 근거

ORD 기록
ord-66f8b8e0129a4557acf0daf67d131c23
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07037938B2

반응 노트

불러오는 중…