Water → HCID 85963598, compound

HRID 1725979Notes

Reaction equation

HRID 1725979 reaction equation
[CH2:1]([C:3]1[C:4]([CH3:22])=[C:5]([C:9]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)(=[O:15])=[O:14])=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])[CH3:2].[Br-:23].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.O>CN(C=O)C>[Br:23][C:10]1[C:9]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)(=[O:15])=[O:14])=[C:5]([C:4]([CH3:22])=[C:3]([CH2:1][CH3:2])[CH:11]=1)[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 23500184Tetra-n-butylammonium tribromideHCID 23647779HCID 23647779, compound

Product 1

HCID 85963598HCID 85963598, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 130B (50 mg, 0.16 mmole) in DMF (5 mL) was added tetra-n-butylammonium tribromide (85 mg, 0.176 mmole), then water (5 mL). After stirring overnight at ambient temperature, the solvents were evaporated and the residue was partitioned between water and ethyl acetate (20 mL each). The two phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic extracts were dried (MgSO4), filtered and concentrated. The residue was purified on a silica gel column eluting with 5% methanol in dichloromethane with 1% acetic acid to provide the desired product, 70 mg (95%). 1H NMR (DMSO-d6) δ 1.2 (t, 3H), 2.04 (s, 3H), 2.55 (q, 2H), 7.15 (s, 1H), 7.25 (t, 1H), 7.68 (d, 1H0, 7.86 (t, 1H), 8.58 (d, 1H), 10.05-13.00 (br s, 2H). MS (ESI(−)) m/e 397, 399 (M−H)−.

Workup

  1. customthe solvents were evaporated
  2. customthe residue was partitioned between water and ethyl acetate (20 mL each)
  3. customThe two phases were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified on a silica gel column
  9. washeluting with 5% methanol in dichloromethane with 1% acetic acid

Sources & evidence

ORD record
ord-af55438acb284730acdb4a0e8d60619b
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

Loading…