HCID 68713207, compound → HCID 11419551, compound

HRID 29273Notes

Reaction equation

HRID 29273 reaction equation
C([O:5][C:6](=[O:39])[C@H:7](C(C)C)[NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]3[O:28][C:29]4[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=4[CH:31]=3)=[O:26])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)(=[O:11])=[O:10])(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[O:28]1[C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[CH:31]=[C:27]1[C:25]([NH:24][C:21]1[CH:22]=[CH:23][C:18]([C:15]2[CH:16]=[CH:17][C:12]([S:9]([NH:8][CH2:7][C:6]([OH:39])=[O:5])(=[O:10])=[O:11])=[CH:13][CH:14]=2)=[CH:19][CH:20]=1)=[O:26]

Participants

4

Reactant 1

HCID 68713207HCID 68713207, compound

Product 1

HCID 11419551HCID 11419551, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

N-({4′-[(1-benzofuran-2-ylcarbonyl)amino]-1,1′-biphenyl-4-yl}sulfonyl)-L-valine t-butyl ester (60 mg) was dissolved in a 95% solution of TFA in methylene chloride (5 mL). The solution was stirred at room temperature for 4 h and the solvent was removed under vacuum. The crude product was triturated with hexane/ethyl acetate (95:5) three times. The product was lyophilized with benzene to give 36 mg of N-({4′-[(1-benzofuran-2-ylcarbonyl)amino]-1,1′-biphenyl-4-yl}sulfonyl)glycine. LCMS MH+ (m/z) 493. 1H NMR (300 MHz, DMSO-d6): δ 10.53 ppm (s, 1H), 7.81-7.54 ppm (m, 11H), 7.34 ppm (dd, 1H, J1=8.4 Hz, J2=8.4 Hz), 7.20 ppm (dd, 1H, J1=8.4 Hz, J2=8.4 Hz), 3.35 ppm (d, 1H J=6.0 Hz), 1.79 ppm (m, 1H), 0.63 ppm (dd, 6H, J1=13.8 Hz, J2=6.6 Hz).

Workup

  1. customthe solvent was removed under vacuum
  2. customThe crude product was triturated with hexane/ethyl acetate (95:5) three times

Sources & evidence

ORD record
ord-f1f60dd0a03346a4a85b8cbab9c2dfd6
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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