Hydrogen Peroxide → trans-(7-Carbamoyl-1,1-diethyl-3-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-carbamic acid tert-butyl ester

HRID 424150Notes

Reaction equation

HRID 424150 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][C@H:8]1[C@H:17]([O:18][CH3:19])[CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:20]#[N:21])=[CH:13][CH:14]=2)[C:9]1([CH2:24][CH3:25])[CH2:22][CH3:23])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=[O:28].[K+].[K+].OO>CS(C)=O.O.C(OC(C)C)(=O)C.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>[C:1]([O:5][C:6](=[O:26])[NH:7][C@H:8]1[C@H:17]([O:18][CH3:19])[CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:20](=[O:28])[NH2:21])=[CH:13][CH:14]=2)[C:9]1([CH2:22][CH3:23])[CH2:24][CH3:25])([CH3:3])([CH3:4])[CH3:2]

Participants

8

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 66673896HCID 66673896, compound

Product 1

HCID 66673985trans-(7-Carbamoyl-1,1-diethyl-3-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-carbamic acid tert-butyl esterYield 104%

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 7915Isopropyl AcetateSolventHCID 656671Sodium PyrosulfiteSolvent

Procedure

To a solution of trans-(7-cyano-1,1-diethyl-3-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid tert-butyl ester (8.5 g, 24 mmol) in DMSO (105 mL) was added K2CO3 (4.98 g, 36 mmol), and the mixture was stirred until all solids were dissolved. To the solution was added 30% hydrogen peroxide (12.2 mL, 120 mmol) in 0.5 mL portions over 45 min at a rate to keep the temperature 30-35° C. The reaction mixture was diluted with water (200 mL) and isopropyl acetate (500 mL), and sodium metabisulfite was added (10 g) to reduce excess peroxides. Layers were separated and the aqueous layer was extracted with isopropyl acetate (3×150 mL) and 10% MeOH/isopropyl acetate (2×100 mL). The combined organic layers were washed with water (3×150 mL) and saturated NaCl (100 mL), dried with Na2SO4 and concentrated to give the title compound (9.4 g). (m/z): [M+H]+ calcd for C21H32N2O4 377.24; found 377.6.

Workup

  1. dissolutionwere dissolved
  2. customthe temperature 30-35° C
  3. additionwas added (10 g)
  4. customLayers were separated
  5. extractionthe aqueous layer was extracted with isopropyl acetate (3×150 mL) and 10% MeOH/isopropyl acetate (2×100 mL)
  6. washThe combined organic layers were washed with water (3×150 mL) and saturated NaCl (100 mL)
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d65e2c452fe84a0cba539292a4dd9343
Source dataset
uspto-grants-2012_01
Patent number
US08101791B2

Reaction notes

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