2,6-Dichlorobenzoyl chloride → HCID 67032576, compound

HRID 920573Notes

Reaction equation

HRID 920573 reaction equation
[C:1]([O:5][C:6](=[O:22])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][O:12][CH:11]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)C(C)C)C.[Cl:32][C:33]1[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[C:34]=1[C:35](Cl)=[O:36]>CC#N>[C:1]([O:5][C:6]([CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][O:12][CH:11]([C:15]2[CH:16]=[CH:17][C:18]([O:21][C:35](=[O:36])[C:34]3[C:33]([Cl:32])=[CH:41][CH:40]=[CH:39][C:38]=3[Cl:42])=[CH:19][CH:20]=2)[CH2:10]1)=[O:22])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 783922,6-Dichlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 666540623-[2-(4-Hydroxy-phenyl)-morpholin-4-yl]-propionic acid tert-butyl ester

Product 1

HCID 67032576HCID 67032576, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-[2-(4-hydroxy-phenyl)-morpholin-4-yl]-propionic acid tert-butyl ester (0.39 g; 1.27 mmol) and N-ethyldiisopropylamine (0.65 mL, 3.81 mmol) in CH3CN (5 mL) was added 2,6-dichlorobenzoyl chloride (0.44 ml; 3.0 mmol), at 0° C. Subsequently, the mixture was allowed to warm to RT and was stirred for 2 days at roomtemperature. The resulting mixture was partitioned between Et2O and 5% aqueous NaHCO3 solution. The layers were separated and the organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O to afford 2,6-dichloro-benzoic acid 4-[4-(2-tert-butoxycarbonyl-ethyl)-morpholin-2-yl]-phenyl ester (0.51 g).

Workup

  1. customat 0° C
  2. customThe resulting mixture was partitioned between Et2O and 5% aqueous NaHCO3 solution
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (SiO2, Et2O

Sources & evidence

ORD record
ord-54d0f179b9614f3dbb22a1a34b13bb0c
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

Loading…