Sodium Hydroxide → HCID 67031880, compound

HRID 920577Notes

Reaction equation

HRID 920577 reaction equation
[C:1]([O:5][C:6](=[O:25])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][O:12][CH:11]([C:15]2[CH:20]=[CH:19][C:18]([S:21][C:22](=O)[CH3:23])=[CH:17][CH:16]=2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[Cl:28][C:29]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])C=1CBr>CCO.O>[C:1]([O:5][C:6](=[O:25])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][O:12][CH:11]([C:15]2[CH:20]=[CH:19][C:18]([S:21][CH2:22][C:23]3[C:29]([Cl:28])=[CH:36][CH:35]=[CH:34][C:33]=3[Cl:37])=[CH:17][CH:16]=2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 301591-Bromomethyl-2,6-dichlorobenzeneHCID 86670014HCID 86670014, compound

Product 1

HCID 67031880HCID 67031880, compoundYield 48.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3-[2-(4-Acetylsulfanyl-phenyl)-morpholin-4-yl]-propionic acid tert-butyl ester (0.31 g; 0.85 mmol) and NaOH (37 mg, 0.93 mmol) in EtOH (10 mL) and water (1 mL) was stirred for 30 min at 0° C. Subsequently, 2,6-dichlorobenzyl bromide (0.22 g; 0.93 mmol), dissolved in EtOH (2.5 mL), was added, and the mixture allowed to warm to RT. After 90 min. the mixture was partitioned between EtOAc and 5% aqueous NaHCO3. The layers were separated, and the organic layer was washed with 5% aqueous NaHCO3 and brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, CH2Cl2/acetone 95:5) to afford 3-{2-[4-(2,6-dichloro-benzylsulfanyl)-phenyl]-morpholin-4-yl}-propionic acid tert-butyl ester (0.20 g).

Workup

  1. additionwas added
  2. temperatureto warm to RT
  3. customAfter 90 min. the mixture was partitioned between EtOAc and 5% aqueous NaHCO3
  4. customThe layers were separated
  5. washthe organic layer was washed with 5% aqueous NaHCO3 and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography (SiO2, CH2Cl2/acetone 95:5)

Sources & evidence

ORD record
ord-44bbf08465924325bf5bb305b2056a6d
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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