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

HRID 723138Notes

Reaction equation

HRID 723138 reaction equation
C([O:3][C:4](=[O:42])[CH2:5][CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([S:22]([C:25]2[CH:29]=[C:28]([C:30]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[NH:31])[S:27][C:26]=2[S:40][CH3:41])(=[O:24])=[O:23])[CH:17]=1)C.O.[OH-].[Li+].Cl>C1COCC1.CO.O>[C:36]([O:35][C:33]([NH:32][C:30](=[NH:31])[C:28]1[S:27][C:26]([S:40][CH3:41])=[C:25]([S:22]([C:18]2[CH:17]=[C:16]([C:10]3[C:11]([CH3:15])=[CH:12][CH:13]=[CH:14][C:9]=3[CH2:8][O:7][CH2:6][CH2:5][C:4]([OH:42])=[O:3])[CH:21]=[CH:20][CH:19]=2)(=[O:24])=[O:23])[CH:29]=1)=[O:34])([CH3:39])([CH3:37])[CH3:38]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 145857715ethyl 3-[[3-methyl-2-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]phenyl]methoxy]propanoate

Product 1

HCID 1458577123-[[3-methyl-2-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]phenyl]methoxy]propanoic acidYield 76.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-{3′-[5-(tert-butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-6-methyl-biphenyl-2-ylmethoxy}-propionic acid ethyl ester (7.0 mg, 11 μmol) in THF (0.5 mL) and MeOH (0.25 mL) was added a solution of lithium hydroxide monohydrate (0.56 mg, 13 μmol) in H2O (50 mL). The mixture was microwaved at 80° C. for 150 seconds, acidified with 0.25 N HCl to ˜pH 3, extracted with EtOAc/DCM (1:1, 3×). The extracts were combined, washed with H2O, dried over Na2SO4, concentrated, and flash chromatographed on silica gel column, eluting with MeOH/DCM (2 to 4%) to give the title compound (5.1 mg, 76% yield) as a white solid.

Workup

  1. customThe mixture was microwaved at 80° C. for 150 seconds
  2. extractionextracted with EtOAc/DCM (1:1, 3×)
  3. washwashed with H2O
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customflash chromatographed on silica gel column
  7. washeluting with MeOH/DCM (2 to 4%)

Sources & evidence

ORD record
ord-3f580c9795f64553ad1afe6144716cfa
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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