Dimethylformamide → HCID 57925827, compound

HRID 1013547Notes

Reaction equation

HRID 1013547 reaction equation
[OH:1][P:2]([C:6]1[CH:7]=[C:8](/[CH:12]=[CH:13]/[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:9]=[CH:10][CH:11]=1)([O:4][CH3:5])=[O:3].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=C[C:31]=2N=N1.CCN(C(C)C)C(C)C.CN(C=O)C>CO>[CH3:5][O:4][P:2]([C:6]1[CH:7]=[C:8](/[CH:12]=[CH:13]/[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:9]=[CH:10][CH:11]=1)([O:1][CH3:31])=[O:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 81531Diisopropylethylamine3×HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate3×HCID 57925997HCID 57925997, compound

Product 1

HCID 57925827HCID 57925827, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-butyl (2E)-3-{3-[hydroxy(methoxy)phosphoryl]phenyl}acrylate was dissolved in methanol (8 ml). BOP (0.4958 g, 1.121 mmol) and Hunig's base (0.2 ml, 1.145 mmol) were added. DMF (2 ml) was added. The reaction was allowed to stir overnight at room temperature. The reaction was not complete. The reaction was partially concentrated under reduced pressure. BOP (0.4836 g, 1.093 mmol) and Hunig's base (0.2 ml, 1.145 mmol) were added. The reaction was allowed to stir. After several hours additional BOP (0.495 g, 1.119 mmol) and Hunig's base (0.2 ml, 1.145 mmol) were added. The reaction was allowed to stir overnight at room temperature. The reaction was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate. The residue was purified by column chromatography on silica gel, eluting with EtOAc/hexane. MS: calc'd 313 (MH+), exp 313 (MH+).

Workup

  1. concentrationThe reaction was partially concentrated under reduced pressure
  2. stirringto stir
  3. stirringto stir overnight at room temperature
  4. concentrationThe reaction was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with saturated aqueous sodium hydrogen carbonate
  7. customThe residue was purified by column chromatography on silica gel
  8. washeluting with EtOAc/hexane

Sources & evidence

ORD record
ord-81eb0cadd34d4d398a5d1ef14463001b
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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