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

HRID 2389720ノート

反応式

HRID 2389720 の反応式
[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]

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3a690ab6a6194cac91a268347ed6e438
出典データセット
uspto-grants-2012_09
特許番号
US08273747B2

反応ノート

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