Lithium Hydroxide → HCID 58189145, compound

HRID 1423136Notes

Reaction equation

HRID 1423136 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)[CH2:29][C:30]([O:32]CC)=[O:31])[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[CH2:28][CH2:29][C:30]([OH:32])=[O:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86652001HCID 86652001, compound

Product 1

HCID 58189145HCID 58189145, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The intermediate (S)-ethyl 3-(2-benzyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)piperazin-1-yl)-3-oxopropanoate (117 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 (97 mg, 88%). LC/MS (Method A) 5.31 min, [M+1]+ 439.

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-8b831f9482b644d49ce9cc1b60395906
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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