Ethyl Acetate → N-[[1-[[[4-(4-Morpholinylmethyl)phenyl]carbonyl]amino]cyclohexyl]carbonyl]-L-methioninal

HRID 1851852Notes

Reaction equation

HRID 1851852 reaction equation
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH:16][C:17]3([C:23]([NH:25][C@H:26]([CH2:31][OH:32])[CH2:27][CH2:28][S:29][CH3:30])=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[O:15])=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH:16][C:17]3([C:23]([NH:25][C@H:26]([CH:31]=[O:32])[CH2:27][CH2:28][S:29][CH3:30])=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[O:15])=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 57672928N-[[1-[[[4-(4-Morpholinylmethyl)phenyl]carbonyl]amino]cyclohexyl]carbonyl]-L-methioninol

Product 1

HCID 57702042N-[[1-[[[4-(4-Morpholinylmethyl)phenyl]carbonyl]amino]cyclohexyl]carbonyl]-L-methioninalYield 85.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under ice-cooling, 356 mg (0.84 mmol) of Des Martin periodinane was added to a solution of 65 mg (0.14 mmol) of N-[[1-[[[4-(4-morpholinylmethyl)phenyl]carbonyl]amino]cyclohexyl]carbonyl]-L-methioninol in 5 ml of methylene chloride, and the mixture was stirred for 1 hour. At the same temperature, 10 ml of ethyl acetate and 10 ml of a saturated aqueous sodium bicarbonate solution were added to the reaction solution. Sodium thiosulfate was added thereto until the solution became transparent, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated brine and dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 55 mg (85%) of the title compound.

Workup

  1. temperatureUnder ice-cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-65936452e1a44452b50150075b35f3ac
Source dataset
uspto-grants-2015_02
Patent number
US08957205B2

Reaction notes

Loading…