Triethylamine → PF-03550096

HRID 1095395노트

반응식

HRID 1095395 반응식
[OH:1][C:2]([CH3:16])([CH3:15])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]1=[O:14].C(N(CC)CC)C.Cl[C:25](OC1C=CC([N+]([O-])=O)=CC=1)=[O:26].[NH2:37][C@H:38]([C:43]([NH2:45])=[O:44])[C:39]([CH3:42])([CH3:41])[CH3:40]>ClCCCl>[NH2:45][C:43]([C@@H:38]([NH:37][C:25]([N:7]1[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:5]([CH2:4][CH2:3][C:2]([OH:1])([CH3:16])[CH3:15])[C:6]1=[O:14])=[O:26])[C:39]([CH3:42])([CH3:41])[CH3:40])=[O:44]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 11297986(2S)-2-Amino-3,3-dimethylbutanamideHCID 57436050HCID 57436050, 화합물

생성물 1

HCID 24857887PF-03550096수율 33.8%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매2회

실험 절차

To a solution of 1-(3-hydroxy-3-methylbutyl)-1,3-dihydro-2H-benzimidazol-2-one (0.25 g, 1.1 mmol) in 1,2-dichloroethane (30 mL) were added triethylamine (0.52 mL, 3.7 mmol) and 4-nitrophenyl chloroformate (0.27 g, 1.4 mmol) at 0° C. and the mixture was stirred for 4 h at rt. Then to this mixture was added a mixture of L-tert-leucinamide (0.18 g, 1.4 mmol) in 1,2-dichloroethane (5 mL) at 0° C. and stirred at rt. After 14 h, the reaction was quenched by addition of water (50 mL) and filtered and washed with water (30 mL) and dichloromethane (30 mL). The obtained solid was suspended in water (50 mL) and filtered. This procedure was repeated twice followed by recrystallization from methanol. The obtained solid was suspended in water (50 mL) again and filtered and this procedure was repeated twice. Then the solid was dissolved in methanol/dichloromethane and filtered and concentrated in vacuo. The obtained solid was then recrystallized from acetone to give 0.14 g (33%) of the title compound.

후처리

  1. additionThen to this mixture was added
  2. stirringstirred at rt
  3. waitAfter 14 h
  4. customthe reaction was quenched by addition of water (50 mL)
  5. filtrationfiltered
  6. washwashed with water (30 mL) and dichloromethane (30 mL)
  7. filtrationfiltered
  8. customThis procedure was repeated twice followed by recrystallization from methanol
  9. filtrationfiltered
  10. dissolutionThen the solid was dissolved in methanol/dichloromethane
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customThe obtained solid was then recrystallized from acetone

출처 및 근거

ORD 기록
ord-3d637b612c864fb2990391ee8f121f34
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138177B2

반응 노트

불러오는 중…