Water → (r)-n-(7-Benzenesulfonyl-chroman-2-ylmethyl)-2-(r)-hydroxy-propionamide

HRID 2355232Notes

Reaction equation

HRID 2355232 reaction equation
[C:1]1([S:7]([C:10]2[CH:19]=[C:18]3[C:13]([CH2:14][CH2:15][CH:16]([CH2:20][NH:21][C:22]([C@H:24]([O:26]C(=O)C)[CH3:25])=[O:23])[O:17]3)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[Li+].[OH-]>CO>[C:1]1([S:7]([C:10]2[CH:19]=[C:18]3[C:13]([CH2:14][CH2:15][C@H:16]([CH2:20][NH:21][C:22](=[O:23])[C@H:24]([OH:26])[CH3:25])[O:17]3)=[CH:12][CH:11]=2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 131728243(r)-Acetic acid 1-[(7-benzenesulfonyl-chroman-2-ylmethyl)-carbamoyl]-ethyl ester

Product 1

HCID 66917474(r)-n-(7-Benzenesulfonyl-chroman-2-ylmethyl)-2-(r)-hydroxy-propionamideYield 542.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-Acetic acid 1-[(7-benzenesulfonyl-chroman-2-ylmethyl)-carbamoyl]-ethyl ester (7.59 mg) was dissolved in 1 mL MeOH, and water (0.25 mL) and LiOH (200 mg) were added. The reaction was stirred at room temperature for two hours, then quenched by addition of water. Crystals formed and were collected by filtration, washed with water and dried under vacuum to give 37 mg of (R)—N-(7-Benzenesulfonyl-chroman-2-ylmethyl)-2-(R)-hydroxy-propionamide. MP=129.5-131.5° C.; MS (M−H)=374.

Workup

  1. customquenched by addition of water
  2. customCrystals formed
  3. filtrationwere collected by filtration
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-1694d3fd0d034a568ca8e01a24927748
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

Loading…