Dicyclohexylcarbodiimide → (5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzyloxy)-acetyl Methanesulfonamide

HRID 11645

反応式

HRID 11645 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH2:15][C:16]([N:18]2[CH2:23][C@H:22]([CH3:24])[N:21]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[CH2:20][C@H:19]2[CH3:33])=[O:17])=[C:6]([CH:13]=1)[CH2:7][O:8][CH2:9][C:10](O)=[O:11].[CH:34]1(N=C=NC2CCCCC2)CCCCC1.C[S:50]([NH2:53])(=[O:52])=[O:51]>ClCCl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH2:15][C:16]([N:18]2[CH2:23][C@H:22]([CH3:24])[N:21]([CH2:25][C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)[CH2:20][C@H:19]2[CH3:33])=[O:17])=[C:6]([CH:13]=1)[CH2:7][O:8][CH:9]([C:10](=[O:11])[CH3:34])[S:50]([NH2:53])(=[O:52])=[O:51]

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 72879MethanesulfonamideHCID 69655258(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzyloxy)-acetic Acid

生成物 1

HCID 86591164(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzyloxy)-acetyl Methanesulfonamide収率 36.8%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of (5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzyloxy)-acetic acid (0.11 g, 0.22 mmol) in dichloromethane (10 mL) was added 4-dimethylaminopyridine (0.04 g, 0.33 mmol) and 1,3-dicyclohexylcarbodiimide (0.049 g, 0.24 mmol). The resulting reaction mixture was stirred at ambient temperature for 20 minutes and then treated with methanesulfonamide (0.025 g, 0.26 mmol). The reaction was stirred at ambient temperature for 18 hours, filtered through a pad of celite and the resulting filter cake was washed with dichloromethane. The combined organics were concentrated in vacuo and purified via chromatography on silica gel to give the title compound (0.045 g, LRMS: 556.2).

後処理

  1. customThe resulting reaction mixture
  2. stirringThe reaction was stirred at ambient temperature for 18 hours
  3. filtrationfiltered through a pad of celite
  4. filtrationthe resulting filter cake
  5. washwas washed with dichloromethane
  6. concentrationThe combined organics were concentrated in vacuo
  7. custompurified via chromatography on silica gel

出典と根拠

ORDレコード
ord-19342639db9b4a3ba8c49da68878b3f5
出典データセット
uspto-grants-2006_08
特許番号
US07098212B2

関連ノート

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