p-Toluenesulfonic acid → HCID 90281991, compound

HRID 1497549Notes

Reaction equation

HRID 1497549 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=O)[CH3:16])=[C:11]([Cl:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:30][CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33]>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([NH:30][CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH3:16])=[C:11]([Cl:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 151417Glycine tert-butyl esterHCID 12463881HCID 12463881, compound

Product 1

HCID 90281991HCID 90281991, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 1-[4-(benzyloxy)-2-chlorophenyl]ethanone (500 mg) and toluene (15.0 mL) were added p-toluenesulfonic acid (110 mg) and tert-butyl glycinate (0.800 mL), followed by heating at 120° C. for 18 hours. After completion, the reaction mixture was left to be cooled, and then concentrated under reduced pressure. To the residue was added methanol (10.0 mL), and the sodium borohydride (90.0 mg) was added there to under ice-cooling, followed by stirring under ice-cooling for 2 hours. To the reaction mixture were added a saturated aqueous ammonium chloride solution and ethyl acetate, and the organic layer was extracted. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain tert-butyl N-{1-[4-(benzyloxy)-2-chlorophenyl]ethyl}glycinate (560 mg).

Workup

  1. waitAfter completion, the reaction mixture was left
  2. temperatureto be cooled
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue was added methanol (10.0 mL)
  5. additionthe sodium borohydride (90.0 mg) was added there to under ice-
  6. temperaturecooling
  7. temperaturecooling for 2 hours
  8. additionTo the reaction mixture were added a saturated aqueous ammonium chloride solution and ethyl acetate
  9. extractionthe organic layer was extracted
  10. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-bf7d41f06fc543e68f8682220b5ddbd3
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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