Hydrochloric Acid → HCID 66611788, compound

HRID 2204719Notes

Reaction equation

HRID 2204719 reaction equation
[Cl:1][C:2]1[C:3]([C:26]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[O:27])=[CH:4][C:5]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:6]([CH:17]=1)[C:7]([O:9]CC1C=CC=CC=1)=[O:8].[Li+].[OH-].O.Cl>O1CCCC1>[Cl:1][C:2]1[C:3]([C:26]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[O:27])=[CH:4][C:5]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:6]([CH:17]=1)[C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 66611998HCID 66611998, compound

Product 1

HCID 66611788HCID 66611788, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

Phenylmethyl 5-chloro-4-(4-morpholinylcarbonyl)-2-[(phenylmethyl)oxy]benzoate (may be prepared as described in Description 66; 381 mg, 0.82 mmol) was redissolved in tetrahydrofuran (4 ml) and LiOH (64 mg, 2.67 mmol) and water (1 ml) were added. The solution was heated at 45° C. for 90 minutes, 2M hydrochloric acid (1.33 ml, 2.66 mmol) was added and the solvent removed in vacuo. The solid was partitioned between 2M HCl (5 ml) and ethyl acetate (40 ml). The organic layer was dried (MgSO4) and the solvent removed in vacuo to give a brown solid. 381 mg.

Workup

  1. customthe solvent removed in vacuo
  2. customThe solid was partitioned between 2M HCl (5 ml) and ethyl acetate (40 ml)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customto give a brown solid

Sources & evidence

ORD record
ord-6cf5feabe7a8455286e7995715077263
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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