3-[[3-methyl-2-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]phenyl]methoxy]propanoic acid → 3-[3'-(5-Carbamimidoyl-2-methylsulfanyl-thiophene-3-sulfonyl)-6-methyl-biphenyl-2-ylmethoxy]-propionic acid

HRID 2216092Notes

Reaction equation

HRID 2216092 reaction equation
C(OC([NH:8][C:9](=[NH:40])[C:10]1[S:14][C:13]([S:15][CH3:16])=[C:12]([S:17]([C:20]2[CH:21]=[C:22]([C:26]3[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:27]=3[CH2:33][O:34][CH2:35][CH2:36][C:37]([OH:39])=[O:38])[CH:23]=[CH:24][CH:25]=2)(=[O:19])=[O:18])[CH:11]=1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[C:9]([C:10]1[S:14][C:13]([S:15][CH3:16])=[C:12]([S:17]([C:20]2[CH:21]=[C:22]([C:26]3[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:27]=3[CH2:33][O:34][CH2:35][CH2:36][C:37]([OH:39])=[O:38])[CH:23]=[CH:24][CH:25]=2)(=[O:19])=[O:18])[CH:11]=1)(=[NH:8])[NH2:40]

Participants

3

Reactant 1

HCID 1458577123-[[3-methyl-2-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]phenyl]methoxy]propanoic acid

Product 1

HCID 218860683-[3'-(5-Carbamimidoyl-2-methylsulfanyl-thiophene-3-sulfonyl)-6-methyl-biphenyl-2-ylmethoxy]-propionic acidYield 70.8%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A mixture of 3-{3′-[5-(tert-butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-6-methyl-biphenyl-2-ylmethoxy}-propionic acid (5.1 mg, 8.4 μmol) in TFA/DCM (1:1, 1.5 mL) was stirred at ambient temperature for 1 h. The mixture was concentrated and flash chromatographed on silica gel, eluting with MeOH/DCM (5 to 12%) to give the title compound (3.0 mg, 69% yield) as a white solid.

Workup

  1. concentrationThe mixture was concentrated
  2. customflash chromatographed on silica gel
  3. washeluting with MeOH/DCM (5 to 12%)

Sources & evidence

ORD record
ord-1d862b3018344de5b4782d36992cde9b
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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