Ethyl Acetate → HCID 46870543, compound

HRID 510518Notes

Reaction equation

HRID 510518 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][CH:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=3)[CH2:10][CH2:9][CH:8]2[NH:18][C:19](=[O:23])[O:20][CH2:21][CH3:22])=[CH:4][CH:3]=1.[H-].[Na+].C(S(O[CH2:35][CH2:36][N:37]([CH3:44])[S:38]([CH2:41][CH2:42][CH3:43])(=[O:40])=[O:39])(=O)=O)CC.C(OCC)(=O)C>CN(C=O)C.C(OCC)(=O)C.C1CCCCC1.O>[CH2:21]([O:20][C:19](=[O:23])[NH:18][CH:8]1[CH2:9][CH2:10][C:11]2[C:16](=[CH:15][C:14]([O:17][CH2:35][CH2:36][N:37]([CH3:44])[S:38]([CH2:41][CH2:42][CH3:43])(=[O:40])=[O:39])=[CH:13][CH:12]=2)[CH:7]1[CH2:6][C:5]1[CH:24]=[CH:25][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH3:22]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 57471221HCID 57471221, compoundHCID 57471222HCID 57471222, compound

Product 1

HCID 46870543HCID 46870543, compound

Reagents, catalysts & solvents 3

HCID 21867204Cyclohexane ethylacetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of ethyl 1-(4-chlorobenzyl)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate (0.128 g, 0.355 mmol) in DMF under N2 was treated with sodium hydride (0.014 g, 0.568 mmol) and the reaction was stirred for 30 minutes at room temperature. A solution of 2-(N-methylpropylsulfonamido)ethyl propane-1-sulfonate (0.102 g, 0.355 mmol) (see step 1) in DMF was added and the reaction mixture was stirred at ambient temperature over night. The mixture was portioned between ethyl acetate and water. The organic layer was washed with water, dried (MgSO4), filtrated and evaporated to afford brown/white crystals. After addition of a few drops of ethyl acetate/cyclohexane (1:4) a white precipitate formed. Yield 43 mg

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature over night
  2. washThe organic layer was washed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltrated
  5. customevaporated
  6. customto afford brown/white crystals
  7. customformed

Sources & evidence

ORD record
ord-56380883cb2240ce9cb62c39db97af24
Source dataset
uspto-grants-2015_08
Patent number
US09096619B2

Reaction notes

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