Potassium Carbonate → 3-(6-{[(4-Chlorophenyl)sulphonyl]amino}-3-{2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl}-5,6,7,8-tetrahydro-1-naphthyl)propanoic acid

HRID 992404ノート

反応式

HRID 992404 の反応式
S(C1C=CC(C)=CC=1)(O)(=O)=O.[F:12][C:13]1[CH:26]=[CH:25][C:16]([C:17]([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[O:18])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([S:40]([NH:43][CH:44]2[CH2:53][CH2:52][C:51]3[C:50]([CH2:54][CH2:55][C:56]([O:58]C)=[O:57])=[CH:49][C:48]([CH2:60][CH2:61]OS(C4C=CC(C)=CC=4)(=O)=O)=[CH:47][C:46]=3[CH2:45]2)(=[O:42])=[O:41])=[CH:36][CH:35]=1>CN(C=O)C>[Cl:33][C:34]1[CH:35]=[CH:36][C:37]([S:40]([NH:43][CH:44]2[CH2:53][CH2:52][C:51]3[C:50]([CH2:54][CH2:55][C:56]([OH:58])=[O:57])=[CH:49][C:48]([CH2:60][CH2:61][N:22]4[CH2:23][CH2:24][CH:19]([C:17](=[O:18])[C:16]5[CH:15]=[CH:14][C:13]([F:12])=[CH:26][CH:25]=5)[CH2:20][CH2:21]4)=[CH:47][C:46]=3[CH2:45]2)(=[O:42])=[O:41])=[CH:38][CH:39]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 15516383Methyl 3-[6-{[(4-chlorophenyl)sulphonyl]amino}-3-(2-{[(4-methylphenyl)sulphonyl]oxy}ethyl)-5,6,7,8-tetrahydro-1-naphthyl]propanoateHCID 73011315(4-Fluorophenyl)(piperidin-4-yl)methanone 4-methylbenzenesulfonate

生成物 1

HCID 155163853-(6-{[(4-Chlorophenyl)sulphonyl]amino}-3-{2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl}-5,6,7,8-tetrahydro-1-naphthyl)propanoic acid

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

6.5 g (17.3 mmol) of 4-(4-fluorobenzoyl)piperidine tosylate and 2.4 g (17.3 mmol) of potassium carbonate are added to a solution of 3.5 g (5.7 mmol) of methyl 3-[6-{[(4-chlorophenyl)sulphonyl]amino}-3-(2-{[(4-methylphenyl)sulphonyl]oxy}ethyl)-5,6,7,8-tetrahydro-1-naphthyl]propanoate, described in Application EP 864 561, in 100 ml of DMF. The reaction mixture is heated at reflux for one hour, then concentrated. The residue is taken up in dichloromethane and washed with water. The organic phase is dried and concentrated and then purified by chromatography on silica gel, using as eluant a dichloromethane/methanol/ammonia mixture (98/2/0.2), to yield the expected compound.

後処理

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for one hour
  3. concentrationconcentrated
  4. washwashed with water
  5. customThe organic phase is dried
  6. concentrationconcentrated
  7. custompurified by chromatography on silica gel

出典と根拠

ORDレコード
ord-dc9f00dc37fe44478fe71273cfe9f469
出典データセット
uspto-grants-2002_10
特許番号
US06469011B2

反応ノート

読み込み中…