Hydrochloric Acid → HCID 53966285, compound

HRID 1900613Notes

Reaction equation

HRID 1900613 reaction equation
[OH-:1].[Li+].[CH2:3]([C:9]1[C:14]([C:15]2[CH:31]=[CH:30][C:18]([O:19][CH:20]3[CH2:24][CH:23]([C:25]([O:27]C)=[O:26])[NH:22][C:21]3=[O:29])=[CH:17][CH:16]=2)=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl>O.O1CCCC1>[C:3]1([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:19][CH:20]([C:21]([OH:29])=[O:1])[CH2:24][C@@H:23]([C:25]([OH:27])=[O:26])[NH2:22])=[CH:30][CH:31]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 22107101HCID 22107101, compound

Product 1

HCID 53966285HCID 53966285, compoundYield 27.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
58 °C

Procedure

A mixture of lithium hydroxide (0.712 g) in water (9.3 ml) and tetrahydrofuran (29 ml) was treated with methyl 3-[4-(6-hexylphenyl)phenoxy]-2-pyrrolidone-5-carboxylate (3.91 g), and heated to 58° C. After about 3.8 hours, the reaction mixture was allowed to cool to room temperature. The reaction mixture was then treated with 5N HCl (5.94 ml). The resulting light suspension was sonicated then stirred at room temperature for fifteen minutes . Insolubles were collected by filtration, washed with 1:1 tetrahydrofuran:water (10 ml), then tetrahydrofuran (10 ml) and finally water (10 ml). The title compound crystallized out from the filtrate and was collected by filtration. This material was dried in vacuo to give 1.077 g of the title compound.

Workup

  1. temperatureto cool to room temperature
  2. customThe resulting light suspension was sonicated
  3. filtrationInsolubles were collected by filtration
  4. washwashed with 1:1 tetrahydrofuran
  5. customThe title compound crystallized out from the filtrate
  6. filtrationwas collected by filtration
  7. customThis material was dried in vacuo

Sources & evidence

ORD record
ord-04679c887d654f33b35e608b2467eb2b
Source dataset
uspto-grants-1996_11
Patent number
US05576323

Reaction notes

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