Citric Acid → HCID 69662937、化合物

HRID 1611849ノート

反応式

HRID 1611849 の反応式
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[S:12]([NH2:15])(=[O:14])=[O:13].[Br:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([Br:37])[C:25]=1[O:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[C:29]([CH:34]([CH3:36])[CH3:35])[CH:28]=1)[C:20](O)=[O:21].CCN(C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl.C1C=CC2N(O)N=NC=2C=1.CN(C)C=O>[Br:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([Br:37])[C:25]=1[O:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[C:29]([CH:34]([CH3:35])[CH3:36])[CH:28]=1)[C:20]([C:6]1[CH:5]=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[OH:1])[C:7]=1[S:12]([NH2:15])(=[O:13])=[O:14])=[O:21]

参加物

9

反応物 5

HCID 311Citric AcidHCID 81531DiisopropylethylamineHCID 870315-Hydroxynaphthalene-1-sulfonamideHCID 2724699PyBOPHCID 9932398HCID 9932398、化合物

生成物 1

HCID 69662937HCID 69662937、化合物収率 54%

試薬・触媒・溶媒 3

HCID 757711-Hydroxybenzotriazole触媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒5 回

反応条件

温度
50 °C

実験手順

To a stirred mixture of 5-hydroxy-1-naphthalenesulphonamide (0.175 mmol) in dichloromethane (0.2 ml) was added a solution of 3,5-dibromo-4-(4-hydroxy-3-isopropylphenoxy)benzoic acid (0.035 mmol), DIEA (0.175 mmol) and dichloromethane (0.2 ml), dimethyl formamide was added to the solution if the sulphonamide not dissolved completely in dichloromethane. After 15 minutes PyBOP (0.042 mmol) and HOBt (0.001 mmol) in dichloromethane (0.3 ml) was added. The reaction mixture was heated at 50° C. for 20 hours. After cooling to room temperature, dichloromethane (1 ml) and citric acid solution (5%, 1 ml) was added and stirred vigorously for 30 min. The organic phase was dried, concentrated and the residue was finally subjected to semi-preparative HPLC (Silica column: 250×20 mm, ethyl acetate/n-heptane (both with 0.5% acetic acid). Gradient: first 2 min 15% ethyl acetate, then over 13 min to 100% ethyl acetate, then additional 5 min 100% ethyl acetate) to give 12 mg (54%) of the title compound.

後処理

  1. temperatureAfter cooling to room temperature
  2. customThe organic phase was dried
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-5182441b89dc4cf4a4a4501adfd5af9b
出典データセット
uspto-grants-2006_01
特許番号
US06989402B1

反応ノート

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