Ethyl Acetate → (R)-4-Amino-6-(4-heptyloxy-phenyl)-4-methyl-hex-1-yn-3-ol

HRID 2076796Notes

Reaction equation

HRID 2076796 reaction equation
[C:1]([CH:3]1[O:7]C(=O)[NH:5][C@@:4]1([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:14][CH:13]=1)[CH3:9])#[CH:2].[OH-].[Na+].CCOC(C)=O.C([O-])(O)=O.[Na+]>C(O)C>[NH2:5][C:4]([CH3:9])([CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:16][CH:17]=1)[C@H:3]([OH:7])[C:1]#[CH:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 86615288(R)-5-Ethynyl-4-[2-(4-heptyloxy-phenyl)-ethyl]-4-methyl-oxazolidin-2-one

Product 1

HCID 86615289(R)-4-Amino-6-(4-heptyloxy-phenyl)-4-methyl-hex-1-yn-3-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of (R)-5-Ethynyl-4-[2-(4-heptyloxy-phenyl)-ethyl]-4-methyl-oxazolidin-2-one in ethanol (1 ml) is added NaOH (1 ml, 1M aqueous solution). The mixture is heated at reflux temperature for 20 hours. The reaction mixture is then poured onto a biphasic mixture of AcOEt and NaHCO3 (saturated aqueous solution). The aqueous phase is extracted with AcOEt (3 times). The combined organic layers are dried (Na2SO4) and concentrated under reduced pressure. The product is purified by RP-HPLC (ZORBAX Extend C-18) eluting with 5%→95% CH3CN in H2O (+0.1% TFA) to give the title compound.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux temperature for 20 hours
  3. extractionThe aqueous phase is extracted with AcOEt (3 times)
  4. dry with materialThe combined organic layers are dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe product is purified by RP-HPLC (ZORBAX Extend C-18)
  7. washeluting with 5%→95% CH3CN in H2O (+0.1% TFA)

Sources & evidence

ORD record
ord-c09e78a6c8de4d79ba4aaf5df008d1c1
Source dataset
uspto-grants-2011_04
Patent number
US07928093B2

Reaction notes

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