Hydrochloric Acid → Methyl 4-(4'-amino-1,1'-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate

HRID 907659

反応式

HRID 907659 の反応式
C([NH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:25])[CH2:17][C:18]([CH3:24])([CH3:23])[C:19]([O:21][CH3:22])=[O:20])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)=O.Cl>CO>[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:25])[CH2:17][C:18]([CH3:23])([CH3:24])[C:19]([O:21][CH3:22])=[O:20])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 21985799Methyl 4-[4'-(formylamino)-1,1'-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoate

生成物 1

HCID 21985743Methyl 4-(4'-amino-1,1'-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate収率 95.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a suspension of methyl 4-[4′-(formylamino)-1,1′-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoate (2.40 g, 7.07 mmol) in 20 mL methanol, was added 7 mL concentrated hydrochloric acid at below rt. The reaction mixture was stirred at rt overnight. The mixture was concentrated under reduced pressure and saturated aqueous sodium bicarbonate solution was slowly added until pH >8.0. The aqueous layer was then extracted with methylene chloride (2×25 mL), and the combined organic layer was dried over sodium sulfate. The mixture was concentrated under reduced pressure to afford methyl 4-(4′-amino-1,1′-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate as a light red solid (2.1 g, 95%). 1H NMR (CDCl3) δ 7.96 (d, J=9 Hz, 2H), 7.60 (d, J=9 Hz, 2H), 7.46 (d, J=9 Hz, 2H), 6.76 (d, J=9 Hz, 2H), 3.85 (br s, 2H), 3.69 (s, 3H), 3.32 (s, 2H), 1.35 (s, 6H); ESI-MS m/z 312.4 (MH+); HRMS m/z calcd for MH+ 312.1594, found 312.1597.

後処理

  1. concentrationThe mixture was concentrated under reduced pressure and saturated aqueous sodium bicarbonate solution
  2. additionwas slowly added until pH >8.0
  3. extractionThe aqueous layer was then extracted with methylene chloride (2×25 mL)
  4. dry with materialthe combined organic layer was dried over sodium sulfate
  5. concentrationThe mixture was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-29018c9ba5594592b04c14a75c89d13d
出典データセット
uspto-grants-2011_09
特許番号
US08013166B2

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