2-Furancarboxylic acid → HCID 67331985, compound

HRID 1672258Notes

Reaction equation

HRID 1672258 reaction equation
[C:1]([O:5][C:6](=[O:33])[CH:7]([NH:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=2)=[CH:22][CH:21]=1)=[O:19])[CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:4])([CH3:3])[CH3:2].[O:34]1[CH:38]=[CH:37][CH:36]=[C:35]1[C:39](O)=[O:40].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[C:1]([O:5][C:6](=[O:33])[CH:7]([NH:17][C:18]([C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:27]=[CH:28][C:29]([NH:32][C:39]([C:35]3[O:34][CH:38]=[CH:37][CH:36]=3)=[O:40])=[CH:30][CH:31]=2)=[CH:24][CH:25]=1)=[O:19])[CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 69192-Furancarboxylic acidHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67333061HCID 67333061, compound

Product 1

HCID 67331985HCID 67331985, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[(4′-Amino-biphenyl-4-carbonyl)-amino]-pentanedioic acid di-tert-butyl ester (350 mg, 0.77 mmol) and 2-Furoic acid (87 mg, 0.77 mmol, 1 equiv.) in DMF (6 mL) was added BOP reagent (409 mg, 0.92 mmol, 1.2 equiv.) and Hunig base (0.16 mL, 0.92 mmol, 1.2 equiv.) under N2. The mixture was stirred at room temperature overnight. Reaction was complete was determined by LC-MS. The reaction mixture was then poured onto cold water. Solid precipitated from the mixture was collected by filtration. The solid was then dissolved in EtOAc, washed with 1N HCl, saturated NaHCO3, and brine, and then dried over MgSO4. After removing the solvent, the solid was dried under vacuum overnight to provide 2-({4′-[(Furan-2-carbonyl)-amino]-biphenyl-4-carbonyl}-amino)-pentanedioic acid di-tert-butyl ester in 87% yield (369 mg). MS (ESI) m/z 549.

Workup

  1. customReaction
  2. customSolid precipitated from the mixture
  3. filtrationwas collected by filtration
  4. dissolutionThe solid was then dissolved in EtOAc
  5. washwashed with 1N HCl, saturated NaHCO3, and brine
  6. dry with materialdried over MgSO4
  7. customAfter removing the solvent
  8. customthe solid was dried under vacuum overnight

Sources & evidence

ORD record
ord-4726b34873f34329bf4cbecd5b3e289d
Source dataset
uspto-grants-2011_08
Patent number
US07998965B2

Reaction notes

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