1-Hydroxybenzotriazole → N-[2,3-Bis(4-chlorophenyl)-1-methylpropyl]-3-hydroxy-2,2-dimethylpropanamide

HRID 1160728ノート

反応式

HRID 1160728 の反応式
Cl.[NH2:2][CH:3]([CH:5]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)[CH3:4].[OH:21][CH2:22][C:23]([CH3:28])([CH3:27])[C:24](O)=[O:25].ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CCOC(C)=O>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([CH:5]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[CH:3]([NH:2][C:22](=[O:21])[C:23]([CH3:28])([CH3:27])[CH2:24][OH:25])[CH3:4])=[CH:19][CH:18]=1

参加物

8

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 785483-Hydroxy-2,2-dimethylpropionic acidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 222704272,3-Bis(4-chlorophenyl)-1-methylpropylamine hydrochloride

生成物 1

HCID 22270540N-[2,3-Bis(4-chlorophenyl)-1-methylpropyl]-3-hydroxy-2,2-dimethylpropanamide

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of 2-amino-3,4-bis(4-chlorophenyl)butane hydrochloride salt (Reference Example 1, Diastereomer a) (3.7 g, 11 mmol), 3-hydroxy-2,2-dimethylpropionic acid (2.0 g, 17 mmol) in CH2Cl2 (100 mL) was added 1-hydroxybenzotriazole (2.3 g, 17 mmol), diisopropylethylamine (7.7 mL, 44 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (3.2 g, 17 mmol). After stirring at room temperature overnight. The reaction mixture was diluted with EtOAc (200 mL), washed with water and saturated aqueous sodium bicarbonate, and concentrated to dryness, and the residue was purified by flash column chromatography on silica gel eluted with 50% EtOAc in hexane to give the title compound. 1H NMR (500 MHz, CD3OD): δ7.24 (d, 2H), 7.12 (d, 2H), 7.10 (d, 2H), 6.92 (d, 2H), 4.25 (m, 1H), 3.68 (ABq, 2H), 3.18 (dd, 1H), 2.93 (ddd, 1H), 2.76 (dd, 1H), 1.20 (s, 3H), 1.19 (s, 3H), 0.96 (d, 3H). LC-MS: m/e 394 (M+H)+ (3.5 min).

後処理

  1. washwashed with water and saturated aqueous sodium bicarbonate
  2. concentrationconcentrated to dryness
  3. customthe residue was purified by flash column chromatography on silica gel
  4. washeluted with 50% EtOAc in hexane

出典と根拠

ORDレコード
ord-1b258c4b6c2548ba946978bb4934fce3
出典データセット
uspto-grants-2010_10
特許番号
US07816534B2

反応ノート

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