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Potassium Carbonate → {3-[(R)-3-((S)-2-Phenyl-propylamino)-butoxy]-phenyl}-acetic Acid Methyl Ester

HRID 902672
Notes
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Reaction equation

HRID 902672 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][C@@H:14](OS(C2C=CC(C)=CC=2)(=O)=O)[CH3:15])[CH:6]=1.[C:28]1([C@H:34]([CH3:37])[CH2:35][NH2:36])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3](=[O:27])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][C@H:14]([NH:36][CH2:35][C@H:34]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH3:37])[CH3:15])[CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1547950(2S)-2-Phenylpropan-1-amineHCID 86598128(S)-{3-[3-(Toluene-4-sulfonyloxy)-butoxy]-phenyl}-acetic acid methyl ester

Product 1

HCID 69254631{3-[(R)-3-((S)-2-Phenyl-propylamino)-butoxy]-phenyl}-acetic Acid Methyl EsterYield 66.2%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

A solution of {3-[(S)-3-(Toluene-4-sulfonyloxy)-butoxy]-phenyl}-acetic acid methyl ester (0.2 g, 0.51 mmol) and (S)-2-Phenyl-propylamine (0.19, 0.77 mmol) in acetonitrile (30 ml) was treated with solid potassium carbonate (0.149, 1.02 mmol). The reaction was heated to reflux and stirred for six days. Upon cooling to room temperature, the reaction was filtered through a pad of celite, washed with EtOAc, and the filtrate was concentrated in vacuo. The crude product was purified by column chromatograph (EtOAc:Hexane/20:80) to give the title compound as an oil (0.12 g, 40%). MS m/e 356.6 (M+H)+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. filtrationthe reaction was filtered through a pad of celite
  4. washwashed with EtOAc
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe crude product was purified by column chromatograph (EtOAc:Hexane/20:80)

Sources & evidence

ORD record
ord-3deb0bc82f264f4fae3aa094ad99fc6e
Source dataset
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07365085B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes