Trifluoroacetic acid → HCID 178454946、化合物

HRID 1809985ノート

反応式

HRID 1809985 の反応式
[C:1](O)(C(F)(F)F)=[O:2].[Cl:8][C:9]1[CH:26]=[CH:25][CH:24]=[CH:23][C:10]=1[CH2:11][O:12][CH2:13][CH2:14][NH:15][C@H:16]1[CH2:21][CH2:20][C@H:19]([CH3:22])[CH2:18][CH2:17]1.C([O:29][C:30](=[O:42])[C:31]([CH3:41])([CH3:40])[CH2:32][S:33][C:34]1[S:38][C:37]([NH2:39])=[N:36][CH:35]=1)C.C1N=CN(C(N2C=NC=C2)=O)C=1.[OH-].[Na+]>C1COCC1.CN(C1C=CN=CC=1)C.C(O)C>[Cl:8][C:9]1[CH:26]=[CH:25][CH:24]=[CH:23][C:10]=1[CH2:11][O:12][CH2:13][CH2:14][N:15]([C@H:16]1[CH2:17][CH2:18][C@H:19]([CH3:22])[CH2:20][CH2:21]1)[C:1](=[O:2])[NH:39][C:37]1[S:38][C:34]([S:33][CH2:32][C:31]([CH3:41])([CH3:40])[C:30]([OH:29])=[O:42])=[CH:35][N:36]=1

参加物

9

反応物 5

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 574814293-(2-Amino-thiazol-5-ylsulfanyl)-2,2-dimethyl-propionic acid ethyl esterHCID 178461337HCID 178461337、化合物

生成物 1

HCID 178454946HCID 178454946、化合物収率 53%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
75 °C

実験手順

The TFA salt of [2-(2-chloro-benzyloxy)-ethyl]-(trans-4-methyl-cyclohexyl)-amine (169 mg, 0.60 mmol) in THF (5 mL) was added 3-(2-amino-thiazol-5-ylsulfanyl)-2,2-dimethyl-propionic acid ethyl ester (195 mg, 0.75 mmol), CDI (243 mg, 1.50 mmol) and DMAP (3.7 mg, 0.03 mmol). The reaction mixture was stirred for 18 h. Ethanol (1 mL) and NaOH (2.5 N, 3 mL, 7.5 mmol) was added and the reaction mixture was heated to 75° C. for 5 h. The mixture was allowed to cool to rt before pH was adjusted (pH<1). The precipitate was filtered off and purified by preparative HPLC to give 170 mg (53%) of 3-{2-[3-[2-(2-Chloro-benzyloxy)-ethyl]-3-(trans-4-methyl-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-2,2-dimethyl-propionic acid.

後処理

  1. temperatureto cool to rt before pH
  2. filtrationThe precipitate was filtered off
  3. custompurified by preparative HPLC

出典と根拠

ORDレコード
ord-f215cdf8b853440ea464de3488b02eee
出典データセット
uspto-grants-2013_01
特許番号
US08362049B2

反応ノート

読み込み中…