Hydrochloric Acid → HCID 66710023, compound

HRID 238190Notes

Reaction equation

HRID 238190 reaction equation
[OH-].[Na+].[CH:3]1([CH:8]([C:22]2[CH:27]=[CH:26][C:25]([CH2:28][N:29]3[C:34](=[O:35])[CH2:33][O:32][C:31]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[N:30]3)=[CH:24][CH:23]=2)[C:9]([NH:11][CH2:12][CH2:13]/[CH:14]=[CH:15]/[C:16]2([C:19]([O-:21])=[O:20])[CH2:18][CH2:17]2)=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4]1.Cl>C1COCC1.C(O)C>[CH:3]1([CH:8]([C:22]2[CH:23]=[CH:24][C:25]([CH2:28][N:29]3[C:34](=[O:35])[CH2:33][O:32][C:31]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[N:30]3)=[CH:26][CH:27]=2)[C:9]([NH:11][CH2:12][CH2:13][CH:14]=[CH:15][C:16]2([C:19]([OH:21])=[O:20])[CH2:18][CH2:17]2)=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86661610HCID 86661610, compound

Product 1

HCID 66710023HCID 66710023, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

86 mg (2.15 mmol) of sodium hydroxide were added to a solution of 120 mg (0.215 mmol) of ethyl cis/trans-1-[4-{[(+)-2-cyclopentyl-2-{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetyl]amino}but-1-en-1-yl]cyclopropanecarboxylate in 0.23 ml of THF and 0.56 ml of ethanol. The suspension was stirred at RT for 20 min and then acidified slightly with 1 N hydrochloric acid. The mixture was extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous ammonium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. This gave 112 mg of the target compound as a cis/trans isomer mixture.

Workup

  1. extractionThe mixture was extracted three times with ethyl acetate
  2. washThe combined organic phases were washed with saturated aqueous ammonium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1360be8a65ee464ebca543078f3f5ff8
Source dataset
uspto-grants-2014_02
Patent number
US08642592B2

Reaction notes

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