Water → HCID 68862804, compound

HRID 1725921Notes

Reaction equation

HRID 1725921 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[C:10]=1[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br-:20].[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:20][C:15]1[C:14]([O:18][CH3:19])=[C:10]([C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:17][CH:16]=1)[C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 15089368HCID 15089368, compoundHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 68862804HCID 68862804, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 151A (730 mg, 2.7 mmol) and tetrabutylammonium tribromide (1.3 g, 2.7 mmol) in DMF (15 mL) was treated dropwise with water (15 mL), stirred for 18 hours, and partitioned between water (250 mL) and ethyl acetate (250 mL). The organic phase was concentrated, diluted with dichloromethane (250 mL), washed with water (7×250 mL) and brine, dried (Na2SO4), filtered, concentrated and purified on silica gel with dichloromethane to provide the desired product. MS (ESI(+)) m/e 363, 365 (M+NH4)+, 368, 370 (M+Na)+; (ESI(−)) m/e 344, 346 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 13.50 (br s, 1H), 8.92 (s, 1H), 7.65 (d, 1H), 7.36 (d, 1H), 3.79 (s, 3H), 1.44 (s, 9H).

Workup

  1. custompartitioned between water (250 mL) and ethyl acetate (250 mL)
  2. concentrationThe organic phase was concentrated
  3. additiondiluted with dichloromethane (250 mL)
  4. washwashed with water (7×250 mL) and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified on silica gel with dichloromethane

Sources & evidence

ORD record
ord-9d9902eb929c46eea7f9bb95930a7cdc
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

Loading…