(S)-2-Phenoxypropionic acid → HCID 86636911, compound

HRID 563877Notes

Reaction equation

HRID 563877 reaction equation
[O:1]([C@@H:8]([CH3:12])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:13]([N:16]([CH:36]([CH3:38])[CH3:37])[CH2:17][CH2:18][CH:19]([C:26]1[CH:31]=[C:30]([CH2:32][CH2:33][OH:34])[CH:29]=[CH:28][C:27]=1[OH:35])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:15])[CH3:14]>C(OCC)(=O)C>[O:1]([C@@H:8]([CH3:12])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:36]([N:16]([CH:13]([CH3:15])[CH3:14])[CH2:17][CH2:18][C@@H:19]([C:26]1[CH:31]=[C:30]([CH2:32][CH2:33][OH:34])[CH:29]=[CH:28][C:27]=1[OH:35])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:38])[CH3:37]

Participants

4

Reactant 2

HCID 775997(S)-2-Phenoxypropionic acidHCID 18357339HCID 18357339, compound

Product 1

HCID 86636911HCID 86636911, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

(S)-2-Phenoxypropionic acid (3.40 g, 20.5 mmol, 1 equiv) was added to a solution of 2-[3-(diisopropylamino)-1-phenylpropyl]-4-(2-hydroxyethyl)phenol (Example 9, 7.28 g, 20.5 mmol, 1 equiv) in ethyl acetate. The mixture was heated at 80° C. for 2 days, upon which the mixture was cooled to room temperature, filtered and washed with ethyl acetate and dried in vacuo at 50° C. overnight to give the title compound as a white solid (3.9 g, 7.48 mmol, 37% yield, 94% ee).

Workup

  1. temperaturewas cooled to room temperature
  2. filtrationfiltered
  3. washwashed with ethyl acetate
  4. customdried in vacuo at 50° C. overnight

Sources & evidence

ORD record
ord-11bdf36c8ff640ec8d8b2da6e78af1e8
Source dataset
uspto-grants-2011_11
Patent number
US08067594B2

Reaction notes

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