Triethylamine → HCID 69655432、化合物

HRID 11641ノート

反応式

HRID 11641 の反応式
[NH2:1][CH2:2][C:3]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:4]=1[O:5][CH2:6][C:7]([N:9]1[CH2:14][C@H:13]([CH3:15])[N:12]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:11][C@H:10]1[CH3:24])=[O:8].C(N(CC)CC)C.CN(C1C=CC=CN=1)C.C([O:48][C:49](=[O:56])[CH:50]([S:52](Cl)(=[O:54])=[O:53])[CH3:51])C>O1CCCC1.C(OCC)(=O)C>[Cl:29][C:27]1[CH:26]=[CH:25][C:4]([O:5][CH2:6][C:7]([N:9]2[CH2:14][C@H:13]([CH3:15])[N:12]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH2:11][C@H:10]2[CH3:24])=[O:8])=[C:3]([CH:28]=1)[CH2:2][NH:1][S:52]([CH:50]([CH3:51])[C:49]([OH:56])=[O:48])(=[O:54])=[O:53]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 122251022-Chlorosulfonyl-propionic acid ethyl esterHCID 54187452(2R,5S)-2-(2-Aminomethyl-4-chloro-phenoxy)-1-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-ethanone

生成物 1

HCID 69655432HCID 69655432、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 2-(2-aminomethyl-4-chloro-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.05 g, 0.119 mmol) in tetrahydrofuran (1 ml) at −40° C. was added triethylamine (0.021 ml, 0.151 mmol), catalytic dimethylaminopyridine and finally a solution of 2-chlorosulfonyl-propionic acid ethyl ester (for preparation, see: Helv. Chim. Acta., (1997) 80, 671 and Bull. Soc. Chim. Fr. (1975), 807) (0.029 g, 0.145 mmol) in tetrahydrofuran (0.25 ml), added over 5 minutes. The reaction was allowed to warm to ambient temperature. After 23 hours the reaction was diluted with ethyl acetate and washed with pH 7 phosphate buffer (0.5 M). The organic layer was dried over magnesium sulfate, filtered and concentrated. The desired product was isolated via silica gel chromatography (0.047 g). This ester (0.07 mmol) was dissolved in 1:1 tetrahydrofuran:water (1 ml) and lithium hydroxide hydrate (5.8 mg, 0.138 mmol) was added. After 21 hours the reaction was concentrated and the title compound obtained after silica gel chromatography (0.039 g, LRMS: 556.1).

後処理

  1. washwashed with pH 7 phosphate buffer (0.5 M)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-23074664ee454d3abe3137f8c295aaf7
出典データセット
uspto-grants-2006_08
特許番号
US07098212B2

反応ノート

読み込み中…