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

HRID 448780Notes

Reaction equation

HRID 448780 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 to the mixture 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 it was 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, and it
  4. dry with materialwas dried with anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d4085b5629904fffa40e7689c49bd709
Source dataset
uspto-grants-2013_07
Patent number
US08481725B2

Reaction notes

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