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 992404노트

반응식

HRID 992404 반응식
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

참가 물질

5

반응물 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

생성물 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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dc9f00dc37fe44478fe71273cfe9f469
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06469011B2

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