Triethylamine → HCID 68861634, compound

HRID 2109403Notes

Reaction equation

HRID 2109403 reaction equation
C(N(CC)CC)C.[C:8]1([C:14]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:17][O:16][C:15]=2[C:25]([OH:27])=O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:28]([O:32][C:33]([NH:35][C:36]1[CH:37]=[C:38]([CH:43]=[CH:44][C:45]=1[O:46][CH3:47])[C:39]([NH:41][NH2:42])=[O:40])=[O:34])([CH3:31])([CH3:30])[CH3:29].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)(Cl)Cl.O.CN(C=O)C>[C:28]([O:32][C:33]([NH:35][C:36]1[CH:37]=[C:38]([CH:43]=[CH:44][C:45]=1[O:46][CH3:47])[C:39]([NH:41][NH:42][C:25]([C:15]1[O:16][CH:17]=[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:14]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:27])=[O:40])=[O:34])([CH3:31])([CH3:30])[CH3:29]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 1502703,4-Diphenyl-2-furoic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 23062411HCID 23062411, compound

Product 1

HCID 68861634HCID 68861634, compoundYield 85.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Triethylamine (5.95 ml) was added dropwise to a mixture of 3,4-diphenyl-2-furancarboxylic acid (compound of Reference Example 33, 3.76 g), 3-(tert-butoxycarbonylamino)-4-methoxybenzoic acid hydrazide (compound of Reference Example 65, 4.00 g), BOP reagent (9.43 g) and DMF (40 ml) at 0° C., and the mixture was stirred overnight at 25° C. After adding water thereto, the reaction solution was diluted with chloroform. The organic layer was then successively washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over MgSO4. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform), thereby giving 6.42 g of the desired compound. Melting point: 137-141° C. (Recrystallized from ethyl acetate/hexane)

Workup

  1. washThe organic layer was then successively washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  2. dry with materialdried over MgSO4
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-a1b58b64cabc41a68b0045079928a782
Source dataset
uspto-grants-2009_04
Patent number
US07514452B2

Reaction notes

Loading…