HCID 57795423, compound → HCID 178499304, compound

HRID 1189998Notes

Reaction equation

HRID 1189998 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([Sn](CCCC)(CCCC)CCCC)=[CH:8][C:9]=1[N:10]([C@H:20]1[CH2:25][CH2:24][C@H:23]([OH:26])[CH2:22][CH2:21]1)[C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[O:4].[O:40]([CH:47]1[CH2:52][CH2:51][C:50](OS(C(F)(F)F)(=O)=O)=[CH:49][CH2:48]1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:50]2[CH2:51][CH2:52][CH:47]([O:40][C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH2:48][CH:49]=2)=[CH:8][C:9]=1[N:10]([C@H:20]1[CH2:21][CH2:22][C@H:23]([OH:26])[CH2:24][CH2:25]1)[C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[O:4]

Participants

5

Reactant 2

HCID 57795423HCID 57795423, compoundHCID 178448220HCID 178448220, compound

Product 1

HCID 178499304HCID 178499304, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a stirred solution of 3-[(trans-4-hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-5-tributylstannanyl-thiophene-2-carboxylic acid methyl ester (150 mg, 0.23 mmol) in toluene (5 mL) were added (PPh3)4Pd (26 mg), CuBr (2 mg, catalytic) and trifluoro-methanesulfonic acid 4-phenoxy-cyclohex-1-enyl ester (87 mg, 0.27 mmol) under nitrogen. The reaction mixture was stirred and heated to reflux during 5 h. The progress of the reaction was monitored by TLC. Filtration and removal of the solvent under reduced pressure on a rotary evaporator followed by silica gel column chromatography using ethyl acetate and hexane (4:1) afforded 3-[(trans-4-hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-5-(4-phenoxy-cyclohex-1-enyl)-thiophene-2-carb-oxylic acid methyl ester (30 mg, 24%) as a syrup.

Workup

  1. temperatureheated
  2. temperatureto reflux during 5 h
  3. filtrationFiltration and removal of the solvent under reduced pressure
  4. customon a rotary evaporator

Sources & evidence

ORD record
ord-eac71f9cbaeb41c093a4e987ad1b07fc
Source dataset
uspto-grants-2014_03
Patent number
US08674118B2

Reaction notes

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