Ammonium Chloride → 4-Amino-5-cyano-2-fluoro-6-methylbiphenyl-3-yl methoxyacetate

HRID 17312ノート

反応式

HRID 17312 の反応式
C(N(C(C)C)CC)(C)C.[NH2:10][C:11]1[C:16]([OH:17])=[C:15]([F:18])[C:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:13]([CH3:25])[C:12]=1[C:26]#[N:27].[CH3:28][O:29][CH2:30][C:31](Cl)=[O:32].[Cl-].[NH4+]>C(OCC)(=O)C>[CH3:28][O:29][CH2:30][C:31]([O:17][C:16]1[C:15]([F:18])=[C:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]([CH3:25])=[C:12]([C:26]#[N:27])[C:11]=1[NH2:10])=[O:32]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 96623Methoxyacetyl chlorideHCID 860974464-Amino-3-cyano-6-fluoro-5-hydroxy-2-methylbiphenyl

生成物 1

HCID 866308254-Amino-5-cyano-2-fluoro-6-methylbiphenyl-3-yl methoxyacetate収率 99%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Diisopropylethylamine (0.64 ml, 3.7 mmol) was added to an ethyl acetate (8 ml) solution of 4-amino-3-cyano-6-fluoro-5-hydroxy-2-methylbiphenyl (I-41) (180 mg, 0.74 mmol), then with cooling with ice, methoxyacetyl chloride (0.17 ml, 1.85 mmol) was added, followed by stirring for 16 hours with gradually heating up to room temperature. Aqueous saturated ammonium chloride solution was added to the reaction liquid, followed by extraction three times with ethyl acetate, the organic layer was washed with saturated sodium bicarbonate water and saturated brine, then dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the resulting residue was subjected to column chromatography, and the eluate with n-hexane:ethyl acetate (1:1) was concentrated under reduced pressure to obtain the entitled compound (229 mg, 99%) as a yellow solid.

後処理

  1. additionwas added
  2. extractionfollowed by extraction three times with ethyl acetate
  3. washthe organic layer was washed with saturated sodium bicarbonate water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration and concentration under reduced pressure
  6. concentrationthe eluate with n-hexane:ethyl acetate (1:1) was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-6543a4d871644d11967d082915b89693
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

反応ノート

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