Water → HCID 71548219, compound

HRID 512930Notes

Reaction equation

HRID 512930 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16]([CH:20]([O:24][CH2:25][CH3:26])[C:21]([OH:23])=[O:22])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.O.C[C@@H](N)C1C=CC=CC=1>CC(C)=O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16]([C@@H:20]([O:24][CH2:25][CH3:26])[C:21]([OH:23])=[O:22])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6431891-Phenethylamine, (+)-HCID 71548220HCID 71548220, compound

Product 1

HCID 71548219HCID 71548219, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred suspension of racemic ethoxy-acid 53 (100 g, 0.27 mol) in acetone:water mixture (9:1, 900 ml) was added a solution of R-(+)-alpha methylbenzylamine (35 ml, 0.27 mol) acetone:water (9:1, 100 ml) in a dropwise manner. The resulting mixture was stirred for 16-17 hours, filtered to separate the solid and neutralise with acetic acid. The process was repeated several times to get (−)-ethoxy acid 54 (18 g, 98-99% e.e by HPLC).

Workup

  1. filtrationfiltered
  2. customto separate the solid
  3. customto get (−)-ethoxy acid 54 (18 g, 98-99% e.e by HPLC)

Sources & evidence

ORD record
ord-cbc192e867c5490a9b6ed6533d580c38
Source dataset
uspto-grants-2015_08
Patent number
US09102665B2

Reaction notes

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