Ammonium Chloride → HCID 67464942, compound

HRID 553996Notes

Reaction equation

HRID 553996 reaction equation
Cl[C:2]([O:4][CH2:5][CH:6]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)=[O:3].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C@H:26]2[NH:31][C@@H:30]([CH2:32][OH:33])[CH2:29][O:28][CH2:27]2)=[CH:22][CH:21]=1.C(=O)(O)[O-].[Na+].[Cl-].[NH4+]>C(Cl)Cl.C(Cl)(Cl)Cl>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C@@H:26]2[CH2:27][O:28][CH2:29][C@H:30]([CH2:32][OH:33])[N:31]2[C:2]([O:4][CH2:5][CH:6]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]3[C:18]2=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:3])=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 343679-Fluorenylmethyl chloroformateHCID 516892Sodium BicarbonateHCID 67463924HCID 67463924, compound

Product 1

HCID 67464942HCID 67464942, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

9-Fluorenylmethyl chloroformate (122 mg) was added to a mixed solution of [(3S,5R)-5-(4-chlorophenyl)morpholin-3-yl]methanol (86 mg) in methylene chloride (3 mL) and a saturated sodium bicarbonate solution (3 mL). The reaction solution was stirred at room temperature for eight hours. Then, chloroform and a saturated ammonium chloride solution were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent solvent: heptane-ethyl acetate system) to obtain 153 mg of the title compound. The property value of the compound is as follows.

Workup

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

Sources & evidence

ORD record
ord-91c6afd3745b4d8484d3fb2db92118b6
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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