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Sodium Hydroxide → HCID 178481285, compound

HRID 1682658
Notes
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Reaction equation

HRID 1682658 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:13][N:12]([CH3:14])[C:11](=[O:15])[N:10]([CH3:16])[CH2:9]2)[CH2:4][CH2:3]1.Br[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].[OH-].[Na+]>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:22]([O:21][C:19]([CH2:18][O:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([N:8]2[CH2:9][N:10]([CH3:16])[C:11](=[O:15])[N:12]([CH3:14])[CH2:13]2)[CH2:6][CH2:7]1)=[O:20])([CH3:25])([CH3:24])[CH3:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 178481284HCID 178481284, compound

Product 1

HCID 178481285HCID 178481285, compoundYield 45.3%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst
HCID 962
Water
Solvent
HCID 1140TolueneSolvent

Procedure

trans-5-(4-Hydroxycyclohexyl)-1,3-dimethylhexahydro-2-oxo-1,3,5-triazine (1.00 g, 4.40 mmol) and t-butyl bromoacetate (1.29 g, 6.60 mmol) were dissolved in toluene (13 ml), and tetra-n-butylammonium hydrogensulfate (45 mg, 0.13 mmol) was added to the mixture. A solution of sodium hydroxide (13.2 g, 330 mmol) dissolved in water (13.2 ml) was dropwise added, and the mixture was stirred at room temperature for 15 hours. The organic layer was partitioned, washed with water and dried over anhydrous magnesium sulfate. After filtration, low boiling matters were distilled away from the filtrate under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/methanol=20/1) to give 680 mg of trans-5-[4-[(t-butoxycarbonyl)methyloxy]cyclohexyl]-1,3-dimethylhexahydro-2-oxo-1,3,5-triazine as a colorless solid

Workup

  1. additionwas dropwise added
  2. customThe organic layer was partitioned
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration, low boiling matters
  6. distillationwere distilled away from the filtrate under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=20/1)

Sources & evidence

ORD record
ord-7785c65010d546dca964caa9b6dbec62
Source dataset
uspto-grants-1997_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05635527

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes