Water → 2-[2-Hydroxy-4-isopropylbenzoylamino]-N-(5-chloropyridin-2-yl)benzamide

HRID 644213ノート

反応式

HRID 644213 の反応式
COC[O:4][C:5]1[CH:29]=[C:28]([CH:30]([CH3:32])[CH3:31])[CH:27]=[CH:26][C:6]=1[C:7]([NH:9][C:10]1[CH:25]=[CH:24][CH:23]=[CH:22][C:11]=1[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=1)=[O:13])=[O:8].C(O)(C(F)(F)F)=O.O>ClCCl>[OH:4][C:5]1[CH:29]=[C:28]([CH:30]([CH3:32])[CH3:31])[CH:27]=[CH:26][C:6]=1[C:7]([NH:9][C:10]1[CH:25]=[CH:24][CH:23]=[CH:22][C:11]=1[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=1)=[O:13])=[O:8]

参加物

5

反応物 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 685343382-[2-methoxymethyloxy-4-isopropylbenzoylamino]-N-(5-chloropyridin-2-yl)benzamide

生成物 1

HCID 685329372-[2-Hydroxy-4-isopropylbenzoylamino]-N-(5-chloropyridin-2-yl)benzamide収率 22%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirring solution of 2-[2-methoxymethyloxy-4-isopropylbenzoylamino]-N-(5-chloropyridin-2-yl)benzamide (5.74 g, 12.6 mmol) in dichloromethane (20 mL) was added TFA (100 mL) followed by water (100 mL). After stirring for 15 min, the solvents were removed in vacuo and the residue was partitioned between ethyl acetate (500 mL) and water (200 mL). At this point, the mixture was filtered to give 1.13 g (22%) of white solid. The filtrate was returned to a separatory funnel and the layers were separated. The organic phase was then washed with 1 M citric acid, once with brine, twice with saturated aq sodium bicarbonate, and once again with brine. The organic phase was then dried with MgSO4, filtered and concentrated to a volume of about 50 mL in vacuo. At this point, a significant amount of precipitate had formed; so the mixture was sonicated and filtered to give another 2.76 g (53%) of the title compound.

後処理

  1. customthe solvents were removed in vacuo
  2. customthe residue was partitioned between ethyl acetate (500 mL) and water (200 mL)
  3. filtrationAt this point, the mixture was filtered

出典と根拠

ORDレコード
ord-d634a7be0ebd4322a14dbd3f2d37353f
出典データセット
uspto-grants-2010_04
特許番号
US07700628B2

反応ノート

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