Benzyl Bromide → HCID 66750789, compound

HRID 643908Notes

Reaction equation

HRID 643908 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([N:20]2[S:24](=[O:26])(=[O:25])[NH:23][C:22](=[O:27])[CH2:21]2)=[CH:11][C:12]2[CH2:13][CH2:14][CH:15]([OH:19])[CH2:16][C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:28]([N:23]1[C:22](=[O:27])[CH2:21][N:20]([C:10]2[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:18][C:17]3[CH2:16][CH:15]([OH:19])[CH2:14][CH2:13][C:12]=3[CH:11]=2)[S:24]1(=[O:26])=[O:25])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 66750740HCID 66750740, compound

Product 1

HCID 66750789HCID 66750789, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(3-benzyloxy-6-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (90 mg, 0.23 mmol) from preparing Example 45, benzyl bromide (0.033 mL, 0.28 mmol) and potassium carbonate (63 mg, 0.46 mmol) in DMF (2 mL) is stirred at RT for 18 h. The mixture is partitioned between EtOAc and 1 N HCl solution. The organic extract is dried with MgSO4 and concentrated. The residue is purified to give the title compound as an oil: (M+NH4)+=478.

Workup

  1. customThe mixture is partitioned between EtOAc and 1 N HCl solution
  2. extractionThe organic extract
  3. dry with materialis dried with MgSO4
  4. concentrationconcentrated
  5. customThe residue is purified

Sources & evidence

ORD record
ord-3180e8833953433f91bcd75c0e9fb485
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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