Triethylamine → Methyl 4-[2-(benzotriazol-1-yloxycarbonyl)-vinyl]-benzoate

HRID 1180801Notes

Reaction equation

HRID 1180801 reaction equation
[C:1]([CH:4]=[CH:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1)([OH:3])=[O:2].CCN(CC)CC.CN([P+](O[N:34]1[N:42]=[N:41][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[NH4+].[Cl-]>CN(C=O)C.CCOC(C)=O>[N:41]1([O:2][C:1]([CH:4]=[CH:5][C:6]2[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=2)=[O:3])[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[N:34]=[N:42]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 86881Benzoic acid, 4-(2-carboxyethenyl)-, methyl esterHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 72479810Methyl 4-[2-(benzotriazol-1-yloxycarbonyl)-vinyl]-benzoateYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution at room temperature of VII (264 mg, 1.28 mmol) in anhydrous DMF (10 ml) under nitrogen were added Et3N (196 μl, 1.41 mmol) and BOP reagent (680 mg, 1.1.54 mmol), respectively. After few min, a precipitate appeared. After 3 h, the reaction mixture was poured into a saturated aqueous solution of NH4Cl, and diluted with AcOEt. After separation, the organic layer was successively washed with sat NH4Cl, H2O and brine, concentrated a little bit, and hexane was added. The suspension was filtered off and rinsed with hexane. The solid was triturated in water, filtered off, rinsed with water, and dried to afford the title compound VIII (346 mg, 1.07 mmol, 84% yield) as a pale yellow solid (not stable on silica gel !). 1H NMR (300 MHz, CDCl3) δ(ppm): 8.56 (d, J=8.3 Hz, 1H), 8.21–8.02 (m, 3H), 7.90–7.72 (m, 4H), 7.62 (t, J=7.4 Hz, 1H), 3.97 (s, 3H).

Workup

  1. customAfter separation
  2. washthe organic layer was successively washed with sat NH4Cl, H2O and brine
  3. concentrationconcentrated a little bit, and hexane
  4. additionwas added
  5. filtrationThe suspension was filtered off
  6. washrinsed with hexane
  7. customThe solid was triturated in water
  8. filtrationfiltered off
  9. washrinsed with water
  10. customdried

Sources & evidence

ORD record
ord-b1cd1211c3ba4805bf348d7d224f7f9b
Source dataset
uspto-grants-2007_10
Patent number
US07282608B2

Reaction notes

Loading…