Hydrochloric Acid → HCID 66611936, compound

HRID 2204713Notes

Reaction equation

HRID 2204713 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:24]=[C:23]([C:25]([N:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)=[O:26])[C:22]([C:33]([F:36])([F:35])[F:34])=[CH:21][C:10]=2[C:11]([O:13]CC2C=CC=CC=2)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[OH-].O.Cl>O1CCCC1>[C:1]1([CH2:7][O:8][C:9]2[CH:24]=[C:23]([C:25]([N:27]3[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]3)=[O:26])[C:22]([C:33]([F:36])([F:34])[F:35])=[CH:21][C:10]=2[C:11]([OH:13])=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 66611240HCID 66611240, compound

Product 1

HCID 66611936HCID 66611936, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of phenylmethyl 2-[(phenylmethyl)oxy]-4-(1-piperidinylcarbonyl)-5-(trifluoromethyl)benzoate (may be prepared as described in Description 57; 170 mg, 0.34 mmol) in tetrahydrofuran (4 ml) was added LiOH (24.55 mg, 1.03 mmol) and water (1 ml). The solution was heated at 45° C. for one hour then room temperature for 18 hours. 2M hydrochloric acid (0.51 ml, 1.03 mmol) was added and the solvent removed in vacuo. The residue was partitioned between ethyl acetate (20 ml) and 2M HCl (10 ml). The organic layer was separated, dried (MgSO4) and the solvent removed in vacuo to give the title compound. 139 mg.

Workup

  1. customthe solvent removed in vacuo
  2. customThe residue was partitioned between ethyl acetate (20 ml) and 2M HCl (10 ml)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-48259f190f52495ca71e096ba7102b76
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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