Tetrabutylammonium Fluoride → 4-[5-[[5-amino-3-methyl-2-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]phenyl]carbamoylamino]pentoxy]benzoic acid

HRID 2216180Notes

Reaction equation

HRID 2216180 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:23][C:24]([NH:26][C:27](=[NH:80])[C:28]1[S:32][C:31]([S:33][CH3:34])=[C:30]([S:35]([C:38]2[CH:39]=[C:40]([C:44]3[C:49]([CH3:50])=[CH:48][C:47]([NH:51]C(OCC[Si](C)(C)C)=O)=[CH:46][C:45]=3[NH:61][C:62](=[O:79])[NH:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][O:69][C:70]3[CH:78]=[CH:77][C:73]([C:74]([OH:76])=[O:75])=[CH:72][CH:71]=3)[CH:41]=[CH:42][CH:43]=2)(=[O:37])=[O:36])[CH:29]=1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>C1COCC1>[NH2:51][C:47]1[CH:48]=[C:49]([CH3:50])[C:44]([C:40]2[CH:41]=[CH:42][CH:43]=[C:38]([S:35]([C:30]3[CH:29]=[C:28]([C:27]([NH:26][C:24]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:25])=[NH:80])[S:32][C:31]=3[S:33][CH3:34])(=[O:37])=[O:36])[CH:39]=2)=[C:45]([NH:61][C:62](=[O:79])[NH:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][O:69][C:70]2[CH:71]=[CH:72][C:73]([C:74]([OH:76])=[O:75])=[CH:77][CH:78]=2)[CH:46]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 1458576514-[5-[[3-methyl-2-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]-5-(2-trimethylsilylethoxycarbonylamino)phenyl]carbamoylamino]pentoxy]benzoic acid

Product 1

HCID 1458576194-[5-[[5-amino-3-methyl-2-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]phenyl]carbamoylamino]pentoxy]benzoic acidYield 128.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutyl ammonium fluoride solution (2.38 mL, 1M in THF) was added to a solution of 4-(5-{3-[3′-[5-(tert-butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-6-methyl-4-(2-trimethylsilanyl-ethoxycarbonylamino)-biphenyl-2-yl]-ureido}-pentyloxy)-benzoic acid (276 mg, 0.298 mmol, Example 283: step d) in THF (10 mL) over 2 days at 35° C. The solvents were removed in vacuo. The residue was diluted in EtOAc, washed with water and brine, and dried over magnesium sulfate. The solvents were removed in vacuo to afford the title compound as a brown solid (300 mg, quantitative). ESI-MS (m/z): Calcd. for C37H44N5O8S3: 782.2 (M+1); found: 781.8.

Workup

  1. customThe solvents were removed in vacuo
  2. additionThe residue was diluted in EtOAc
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-287c9fc9e97e4a95ab7ee10a95d586cd
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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