Lithium Hydroxide → HCID 52918528, compound

HRID 1423135Notes

Reaction equation

HRID 1423135 reaction equation
[CH2:1]([C@H:8]1[CH2:13][N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:10][N:9]1[C:28](=[O:36])[CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-]>C1COCC1.O>[CH2:1]([C@H:8]1[CH2:13][N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:10][N:9]1[C:28](=[O:36])[CH2:29][CH2:30][C:31]([OH:33])=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86652000HCID 86652000, compound

Product 1

HCID 52918528HCID 52918528, compoundYield 70.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The intermediate (S)-ethyl 4-(2-benzyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)piperazin-1-yl)-4-oxobutanoate (124 mg, 0.25 mmol) was dissolved in THF (4 mL) and treated with LiOH (12 mg, 0.5 mmol) in water (1 mL) and stirred for 24 h. The reaction mixture was evaporated to half-volume, diluted with water (5 mL) and the pH adjusted to pH ˜7 with a 1 N solution of hydrochloric acid. The resulting precipitate was filtered with the aid of water and air dried to afford the title compound as a solid (82 mg, 70%). LC/MS (Method A) 6.72 min, [M+1]+ 467.

Workup

  1. customThe reaction mixture was evaporated to half-volume
  2. additiondiluted with water (5 mL)
  3. filtrationThe resulting precipitate was filtered with the aid of water and air
  4. customdried

Sources & evidence

ORD record
ord-ebfeae0daf16417ba737f5ed37120861
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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