[2-tert-Butoxycarbonylamino-2-(4-fluoro-phenyl)-ethylsulfanyl]-acetic acid methyl ester → 5-(4-Fluoro-phenyl)-thiomorpholin-3-one

HRID 539621Notes

Reaction equation

HRID 539621 reaction equation
COC(=O)[CH2:4][S:5][CH2:6][CH:7]([NH:15][C:16]([O:18]C(C)(C)C)=O)[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1>FC(F)(F)C(O)=O>[F:14][C:11]1[CH:12]=[CH:13][C:8]([CH:7]2[NH:15][C:16](=[O:18])[CH2:4][S:5][CH2:6]2)=[CH:9][CH:10]=1

Participants

3

Reactant 1

HCID 58200302[2-tert-Butoxycarbonylamino-2-(4-fluoro-phenyl)-ethylsulfanyl]-acetic acid methyl ester

Product 1

HCID 582002835-(4-Fluoro-phenyl)-thiomorpholin-3-oneYield 100.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of [2-tert-butoxycarbonylamino-2-(4-fluoro-phenyl)-ethylsulfanyl]-acetic acid methyl ester (3.23 g, 9.4 mmol) in trifluoroacetic acid (10 mL) was stirred at 50° C. for 10 hours. The solution was then concentrated under reduced pressure, and the residue was partitioned between saturated aqueous sodium bicarbonate and dichloromethane. The organic layer was separated, dried (Na2SO4), filtered and concentrated under reduced pressure to give 2.0 g of 5-(4-fluoro-phenyl)-thiomorpholin-3-one, MP=111-112° C.

Workup

  1. concentrationThe solution was then concentrated under reduced pressure
  2. customthe residue was partitioned between saturated aqueous sodium bicarbonate and dichloromethane
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-639b13e750a24b7a958ef592185abbcf
Source dataset
uspto-grants-2014_10
Patent number
US08871760B2

Reaction notes

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