Lithium Hydroxide → HCID 131723211, compound

HRID 8847Notes

Reaction equation

HRID 8847 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([CH2:17][C@H:18]([CH3:29])[C:19]([O:21]CC2C=CC=CC=2)=[O:20])(=[O:16])=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-]>CO>[CH2:1]([C@@:18]([CH3:29])([CH2:17][S:14]([N:11]1[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][CH2:10]1)(=[O:16])=[O:15])[C:19]([OH:21])=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 131723212HCID 131723212, compound

Product 1

HCID 131723211HCID 131723211, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 100 mL round bottom flask equipped with magnetic stirring bar and N2 inlet was charged with 3.0 g benzyl 3-(4-benzylpiperizin-1-ylsulfonyl)-2(R)-methylpropionate, 1.2 g LiOH (4 eq.) in 20 mL 50% aqueous methanol. After 2 hours HPLC analysis showed no starting material. The reaction was concentrated to half volume and partitioned between Et2O and H2O. The aqueous layer was acidified to pH 5 and extracted with 2×75 mL ethyl acetate. The combined organics were dried, and concentrated in vacuo to yield 550 mg (25%) white solid.

Workup

  1. customA 100 mL round bottom flask equipped with magnetic stirring bar and N2 inlet
  2. concentrationThe reaction was concentrated to half volume
  3. custompartitioned between Et2O and H2O
  4. extractionextracted with 2×75 mL ethyl acetate
  5. customThe combined organics were dried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-23f9c4ecd6c3478fab0005d763040104
Source dataset
uspto-grants-2006_08
Patent number
US07091219B2

Reaction notes

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