Hydrochloric Acid → HCID 67459992, compound

HRID 553997Notes

Reaction equation

HRID 553997 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[NH:13][C@@H:12]([CH:14]=[CH:15][C:16]([O:18][CH3:19])=[O:17])[CH2:11][O:10][CH2:9]2)=[CH:4][CH:3]=1.[CH:20]([CH2:22][C:23](O)=[O:24])=[CH2:21].O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.Cl>C1COCC1.C(OCC)(=O)C>[C:23]([N:13]1[C@H:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:9][O:10][CH2:11][C@@H:12]1/[CH:14]=[CH:15]/[C:16]([O:18][CH3:19])=[O:17])(=[O:24])[CH2:22][CH:20]=[CH2:21].[C:23]([N:13]1[C@H:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:9][O:10][CH2:11][C@@H:12]1/[CH:14]=[CH:15]\[C:16]([O:18][CH3:19])=[O:17])(=[O:24])[CH2:22][CH:20]=[CH2:21]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 327433-Butenoic acidHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 67462988HCID 67462988, compound

Product 2

HCID 67459992HCID 67459992, compoundHCID 67460813HCID 67460813, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

TEA (88.4 μL) was added to a solution of methyl 3-[(3S,5R)-5-(4-chlorophenyl)morpholin-3-yl]acrylate (89 mg), vinylacetic acid (40.4 μL), and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (121 mg) in THF (4 mL) at room temperature. The reaction solution was stirred at room temperature for two hours. Then, a 1 N hydrochloric acid solution and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was sequentially washed with a 1 N sodium hydroxide solution and brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 52.8 mg of methyl 3-[(3S,5R)-4-(3-butenoyl)-5-(4-chlorophenyl)morpholin-3-yl]-(E)-acrylate and 35.1 mg of methyl 3-[(3S,5R)-4-(3-butenoyl)-5-(4-chlorophenyl)morpholin-3-yl]-(Z)-acrylate. The property values of the isomers are as follows.

Workup

  1. customthe organic layer was separated
  2. washThe resulting organic layer was sequentially washed with a 1 N sodium hydroxide solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-3954c8e00a69435087a17fec3e7e3a9d
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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