Hydrochloric Acid → 4-{[(4-Tert-butylcyclohexyl)(1-{2-hydroxyethyl}-1h-benzimidazol-2-yl)-amino]methyl}benzoic acid

HRID 229994노트

반응식

HRID 229994 반응식
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([N:11]([CH2:28][C:29]2[CH:38]=[CH:37][C:32]([C:33]([O:35]C)=[O:34])=[CH:31][CH:30]=2)[C:12]2[N:16]([CH2:17][CH2:18][O:19][Si](C)(C)C)[C:15]3[CH:24]=[CH:25][CH:26]=[CH:27][C:14]=3[N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].CCOC(C)=O.Cl>O1CCOCC1.O>[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([N:11]([CH2:28][C:29]2[CH:30]=[CH:31][C:32]([C:33]([OH:35])=[O:34])=[CH:37][CH:38]=2)[C:12]2[N:16]([CH2:17][CH2:18][OH:19])[C:15]3[CH:24]=[CH:25][CH:26]=[CH:27][C:14]=3[N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 68838381Methyl 4-{[(4-tert-butylcyclohexyl)(1-{2-[(trimethylsilyl)oxy]ethyl}-1H-benz-imidazol-2-yl)amino]methyl}benzoate

생성물 1

HCID 688378984-{[(4-Tert-butylcyclohexyl)(1-{2-hydroxyethyl}-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 10 Step A (0.13 mmol, 73 mg) in 2 mL of dioxane was added a solution of LiOH (1.25 mmol, 30 mg) in 1 mL of H2O. The resulting solution was stirred at 40° C. overnight. The reaction mixture was taken up in a pH 7 buffer solution and EtOAc. The mixture was acidified with 2 N HCl until two clear layers formed after agitation. The organic layer was collected and the aqueous layer was washed with EtOAc. The combined organic layers were dried with MgSO4 and concentrated under reduced pressure to afford the acid as a beige solid. MS (ESI): m/z 450 (M+H). HPLC A: 2.05 min.

후처리

  1. customformed after agitation
  2. customThe organic layer was collected
  3. washthe aqueous layer was washed with EtOAc
  4. dry with materialThe combined organic layers were dried with MgSO4
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-44d32c51ee8748bba403130a7731057d
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563815B2

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