4-(2-(2-Ethoxycarbonyl-ethyl)-3-{6-[3-methanesulfonyl-5-(2-methylsulfanyl-pyrimidin-4-yl)-phenoxy]-hexyl}-phenoxy)-butyric acid ethyl ester → 4-{2-(2-Ethoxycarbonyl-ethyl)-3-[6-(3-methanesulfonyl-5-pyrimidin-4-yl-phenoxy)-hexyl]-phenoxy}-butyric Acid Ethyl Ester

HRID 418071Notes

Reaction equation

HRID 418071 reaction equation
[CH2:1]([O:3][C:4](=[O:47])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([C:28]3[CH:33]=[CH:32][N:31]=[C:30](SC)[N:29]=3)[CH:25]=[C:24]([S:36]([CH3:39])(=[O:38])=[O:37])[CH:23]=2)[C:10]=1[CH2:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH3:2]>CO.C1COCC1.[Ni]>[CH2:1]([O:3][C:4](=[O:47])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([C:28]3[CH:33]=[CH:32][N:31]=[CH:30][N:29]=3)[CH:25]=[C:24]([S:36]([CH3:39])(=[O:38])=[O:37])[CH:23]=2)[C:10]=1[CH2:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH3:2]

Participants

5

Reactant 1

HCID 578630834-(2-(2-Ethoxycarbonyl-ethyl)-3-{6-[3-methanesulfonyl-5-(2-methylsulfanyl-pyrimidin-4-yl)-phenoxy]-hexyl}-phenoxy)-butyric acid ethyl ester

Product 1

HCID 578631174-{2-(2-Ethoxycarbonyl-ethyl)-3-[6-(3-methanesulfonyl-5-pyrimidin-4-yl-phenoxy)-hexyl]-phenoxy}-butyric Acid Ethyl Ester

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-(2-ethoxycarbonyl-ethyl)-3-{6-[3-methanesulfonyl-5-(2-methylsulfanyl-pyrimidin-4-yl)-phenoxy]-hexyl}-phenoxy)-butyric acid ethyl ester (292 mg, 0.423 mmol) in MeOH (15 ml) and THF (15 mL), Raney Ni (2 mL) was added, and stirred at r.t. for 3 h. The reaction was filtered, the residue was washed with MeOH, concentration gave an oil which was used in the next step without further purification. (164 mg).

Workup

  1. filtrationThe reaction was filtered
  2. washthe residue was washed with MeOH, concentration
  3. customgave an oil which
  4. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-bf3cc176bff24119a7ef49e445eaa731
Source dataset
uspto-grants-2012_01
Patent number
US08093253B2

Reaction notes

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