Hydrochloric Acid → 3-Bromo-4-{[(4-tert-butylcyclohexyl)(5-methoxy-1-methyl-1h-benzimidazol-2-yl)amino]methyl}benzoic acid

HRID 230017노트

반응식

HRID 230017 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][N:13]([CH:26]1[CH2:31][CH2:30][CH:29]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:28][CH2:27]1)[C:14]1[N:18]([CH3:19])[C:17]2[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:16]=2[N:15]=1)[C:5]([O:7]C)=[O:6].[Li+].[OH-].CCOC(C)=O.Cl>O1CCOCC1.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][N:13]([CH:26]1[CH2:27][CH2:28][CH:29]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:30][CH2:31]1)[C:14]1[N:18]([CH3:19])[C:17]2[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:16]=2[N:15]=1)[C:5]([OH:7])=[O:6]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 68837491Methyl 3-bromo-4-{[(4-tert-butylcyclohexyl)(5-methoxy-1-methyl-1H-benz-imidazol-2-yl)amino]methyl}benzoate

생성물 1

HCID 688388153-Bromo-4-{[(4-tert-butylcyclohexyl)(5-methoxy-1-methyl-1h-benzimidazol-2-yl)amino]methyl}benzoic acid

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
40 °C

실험 절차

To the title compound of Example 224 Step D (0.07 mmol, 40 mg) in 2 mL of dioxane was added a solution of LiOH (1 mmol, 24 mg) in 1 mL of H2O. The reaction was allowed to stir at 40° C. for 1.5 h. The crude reaction mixture was poured into pH 7 buffer/EtOAc, which was acidified with 2 N HCl until two clear layers formed after agitation. The organic phase was collected and the aqueous phase was extracted twice with EtOAc. The combined organic phase was dried over Na2SO4, then concentrated under reduced pressure to afford the product as a slightly yellow-green foam. HPLC A: 2.32 min.

후처리

  1. customThe crude reaction mixture
  2. customformed after agitation
  3. customThe organic phase was collected
  4. extractionthe aqueous phase was extracted twice with EtOAc
  5. dry with materialThe combined organic phase was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto afford the product as a slightly yellow-green foam
  8. custom2.32 min.

출처 및 근거

ORD 기록
ord-4776b4418b33418490a2decccacea137
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563815B2

반응 노트

불러오는 중…