Benzenesulfonyl chloride → 4'-[(5-benzenesulfonylamino-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonyl-L-valine

HRID 29276Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][C:22]([S:25]([NH:28][C@H:29]([C:33]([OH:35])=[O:34])[CH:30]([CH3:32])[CH3:31])(=[O:27])=[O:26])=[CH:21][CH:20]=4)=[CH:15][CH:14]=3)=[O:11])=[CH:7][C:6]=2[CH:36]=1.[C:37]1([S:43](Cl)(=[O:45])=[O:44])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>>[C:37]1([S:43]([NH:1][C:2]2[CH:3]=[CH:4][C:5]3[O:9][C:8]([C:10]([NH:12][C:13]4[CH:18]=[CH:17][C:16]([C:19]5[CH:20]=[CH:21][C:22]([S:25]([NH:28][C@H:29]([C:33]([OH:35])=[O:34])[CH:30]([CH3:32])[CH3:31])(=[O:26])=[O:27])=[CH:23][CH:24]=5)=[CH:15][CH:14]=4)=[O:11])=[CH:7][C:6]=3[CH:36]=2)(=[O:45])=[O:44])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

Reactant 2

HCID 7369Benzenesulfonyl chloride

HCID 44397439HCID 44397439, compound

Product 1

HCID 443974574'-[(5-benzenesulfonylamino-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonyl-L-valine

Procedure

N-[(4′-{[(5-amino-1-benzofuran-2-yl)carbonyl]amino}-1,1′-biphenyl-4-yl)sulfonyl]-L-valine-Wang resin (0.3 g), from Example 7, was sulfonylated with benzenesulfonyl chloride according to the procedure of Example 8 followed by cleavage from the resin to provide 4′-[(5-benzenesulfonylamino-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonyl-L-valine. LCMS MH+ (m/z) 648. 1H NMR (300 MHz, CD3OD): δ 7.92-7.69 ppm (m, 9H), 7.58-7.43 ppm (m, 6H), 7.22-7.18 ppm (dd, 2H, J1=9.0 Hz, J2=2.5 Hz), 3.64 ppm (d, 1H, J=5.0 Hz), 2.09-2.01 ppm (m, 1H), 0.97 ppm (d, 3H, J=7.0 Hz), 0.90 ppm (d, 3H, J=7.0 Hz).

Sources & evidence

ORD record: ord-b6c6c00c8c424457a715a380f01369bc
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07420001B2

Reaction notes

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