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 992404Notes

Reaction equation

HRID 992404 reaction equation
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

Participants

5

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-dc9f00dc37fe44478fe71273cfe9f469
Source dataset
uspto-grants-2002_10
Patent number
US06469011B2

Reaction notes

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