Hydrochloric Acid → HCID 135979888, compound

HRID 1672707Notes

Reaction equation

HRID 1672707 reaction equation
[C:1]([C:5]1[CH:46]=[CH:45][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2/[CH:17]=[CH:18]/[CH:19]([CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]3[NH:43][C:42](=[O:44])[O:41][N:40]=3)=[CH:35][CH:34]=2)[CH2:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27]C)=[O:26])=[CH:23][CH:22]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].C(OCC)C.Cl>C1COCC1.O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2/[CH:17]=[CH:18]/[CH:19]([CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]3[NH:43][C:42](=[O:44])[O:41][N:40]=3)=[CH:35][CH:34]=2)[CH2:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=2)=[CH:45][CH:46]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 3939Lithium HydroxideHCID 135978828HCID 135978828, compound

Product 1

HCID 135979888HCID 135979888, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 500 mg (0.81 mmol) of methyl 4-((3E)-4-{2-[(4-tert-butylbenzyl)oxy]phenyl}-2-{2-[4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl]ethyl}but-3-en-1-yl)benzoate in 5 ml of THF and 5 ml of water is mixed with 38.8 mg (1.62 mmol) of lithium hydroxide and stirred at 50° C. for 12 h. Cooling is followed by addition of water and extraction with diethyl ether. The aqueous phase is acidified with 1 M hydrochloric acid and extracted with diethyl ether. The resulting organic phase is washed with sodium chloride solution, dried over sodium sulfate and concentrated. 420 mg (0.7 mmol, 79% of theory) of the title compound are obtained.

Workup

  1. temperatureCooling
  2. extractionextracted with diethyl ether
  3. washThe resulting organic phase is washed with sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6c9437959a874fcf9f0766b94704c052
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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