Acetic Acid → 3-{[4-(BOC-methyl-amino)-cyclohexylamino]-methyl}-4-fluoro-benzene boronic acid

HRID 2389720노트

반응식

HRID 2389720 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][C:3]=1[CH:11]=O.[C:13]([O:17][C:18](=[O:27])[NH:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([NH2:26])[CH2:22][CH2:21]1)([CH3:16])([CH3:15])[CH3:14].[CH3:28]C(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C1COCC1.C1(C)C=CC=CC=1.CCOC(C)=O>[C:18]([N:19]([CH3:28])[CH:20]1[CH2:21][CH2:22][CH:23]([NH:26][CH2:11][C:3]2[CH:4]=[C:5]([B:8]([OH:9])[OH:10])[CH:6]=[CH:7][C:2]=2[F:1])[CH2:24][CH2:25]1)([O:17][C:13]([CH3:16])([CH3:14])[CH3:15])=[O:27]

참가 물질

9

반응물 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 2778651(4-Fluoro-3-formylphenyl)boronic acidHCID 5049666Sodium triacetoxyborohydrideHCID 178419079HCID 178419079, 화합물

생성물 1

HCID 597669043-{[4-(BOC-methyl-amino)-cyclohexylamino]-methyl}-4-fluoro-benzene boronic acid

시약·촉매·용매 3

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-fluoro-3-formyl benzene boronic acid (0.88 g, 5.99 mmol) in THF (5 mL) and toluene (5 mL) was added amine (3) (1.4 g, 7.19 mmol) followed by AcOH (0.34 mL, 7.19 mmol), and the resulting solution was stirred at RT for 18 h. After this time sodium triacetoxyborohydride (1.57 g, 8.38 mmol) was added and the resulting solution was stirred at RT for a further 6 h. EtOAc (10 mL) was added to the reaction mixture followed by dropwise addition of sat. NaHCO3 solution (10 mL). The organic layer was separated and the aqueous layer was extracted into EtOAc (2×10 mL). The combined organic layers were dried (MgSO4), filtered and reduced in vacuo to give the title compound as a yellow solid.

후처리

  1. stirringthe resulting solution was stirred at RT for a further 6 h
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted into EtOAc (2×10 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered

출처 및 근거

ORD 기록
ord-3a690ab6a6194cac91a268347ed6e438
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273747B2

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