Hydrochloric Acid → HCID 54115854, compound

HRID 1900625Notes

Reaction equation

HRID 1900625 reaction equation
[OH-:1].[Li+].[C:3]1([CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:29]=[CH:28][C:16]([O:17][CH:18]3[CH2:22][CH:21]([C:23]([O:25]C)=[O:24])[NH:20][C:19]3=[O:27])=[CH:15][CH:14]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl>O.O1CCCC1>[C:3]1([CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:29]=[CH:28][C:16]([O:17][CH:18]([C:19]([OH:1])=[O:27])[CH2:22][C@@H:21]([C:23]([OH:25])=[O:24])[NH2:20])=[CH:15][CH:14]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 22107148HCID 22107148, compound

Product 1

HCID 54115854HCID 54115854, compoundYield 28.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of lithium hydroxide (0.072 g) in water (0.9 ml) and tetrahydrofuran (2.9 ml) was treated with methyl 3-[4-(4-phenylbutyl) phenoxy]-2-pyrrolidone-5-carboxylate (0.370 g), and heated to 60° C. After about 4.0 hours, the reaction mixture was allowed to cool to room temperature. After approximately 2.25 hours at room temperature, the reaction mixture was treated with 5N HCl (604 ml). The resulting biphasic solution was cooled to 5° C. for approximately 18 hours. The biphasic solution was treated with water (2 ml). The resulting milky solution was sonicated resulting in crystal formation. The crystals were collected by filtration, washed with 1:1 THF:water (10 ml), THF (10 ml), and water (10 ml). The crystals were then dried overnight in at vacuum oven at 60° C. to afford the title compound (106 mg).

Workup

  1. temperatureto cool to room temperature
  2. waitAfter approximately 2.25 hours at room temperature
  3. temperatureThe resulting biphasic solution was cooled to 5° C. for approximately 18 hours
  4. customThe resulting milky solution was sonicated
  5. customresulting in crystal formation
  6. filtrationThe crystals were collected by filtration
  7. washwashed with 1:1 THF
  8. customThe crystals were then dried overnight in at vacuum oven at 60° C.

Sources & evidence

ORD record
ord-1b172e63ef0e4f2d85bfdef736f6f821
Source dataset
uspto-grants-1996_11
Patent number
US05576323

Reaction notes

Loading…