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

HRID 1987302노트

반응식

HRID 1987302 반응식
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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-470187f6825c41cabe2b8a2e5c1eee4a
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07550489B2

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