Water → HCID 22490120, compound

HRID 2179930Notes

Reaction equation

HRID 2179930 reaction equation
C[O:2][C:3]([C:5]1[O:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]([CH:32]([C:40]([O:42]C)=[O:41])[CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[S:18]([C:21]3[C:26]([CH3:27])=[CH:25][C:24]([O:28][CH3:29])=[C:23]([CH3:30])[C:22]=3[CH3:31])(=[O:20])=[O:19])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)=[O:4].[Li+].[OH-].O>C1COCC1.O.CO>[C:40]([CH:32]([N:17]([CH2:16][C:13]1[CH:14]=[CH:15][C:10]([C:7]2[O:6][C:5]([C:3]([OH:4])=[O:2])=[CH:9][CH:8]=2)=[CH:11][CH:12]=1)[S:18]([C:21]1[C:26]([CH3:27])=[CH:25][C:24]([O:28][CH3:29])=[C:23]([CH3:30])[C:22]=1[CH3:31])(=[O:20])=[O:19])[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([OH:42])=[O:41]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 86590427HCID 86590427, compound

Product 1

HCID 22490120HCID 22490120, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a stirred solution of 5-(4-{[(1-Methoxycarbonyl-2-phenyl-ethyl)-(4-methoxy-2,3,6-trimethyl-benzenesulfonyl)-amino]-methyl}-phenyl)-furan-2-carboxylic acid methyl ester (16 mg, 0.026 mmol.) in THF:H2O:MeOH (3:1:2) (1 ml.), was added LiOH in water (1N) (0.2 ml. 0.26 mmol.). The reaction mixture was stirred at room temperature during 1 hr. TLC monitored the progress of the reaction. When the reaction was completed, the mixture was concentrated under reduced pressure on a rotary evaporator. The residue was treated with a solution 20% of KHSO4 and extracted in EtOAc. The EtOAc layer was dried over Na2SO4. Filtration and removal of the solvent under reduced pressure on a rotary evaporator followed by silica chromatography using 90% EtOAc, 10% MeOH and 1 drop of AcOH, afforded 5-(4-{[(1-Carboxy-2-phenyl-ethyl)-(4-methoxy-2,3,6-trimethyl-benzenesulfonyl)-amino]-methyl}-phenyl)-furan-2-carboxylic acid. 1HNMR (Varian 400 MHz, DMSO) δ7.37 (d, 2H, J=8.5 Hz, HPh), 7.27 (d, 2H, J=8.3 Hz, HPh), 7.13 (m, 6H, HPh), 6.69 (d, 1H, J=3.2 Hz, furanH), 6.58 (d, 1H, J=3.2 Hz, furanH), 6.50 (s, 1H, MTRH), 4.81 (d, 1H, J=15.5 Hz, NCH2Ph), 4.41 (d, 1H, J=15.9 Hz, NCH2Ph), 4.06 (dd, 1H, J=3.5 and 9.5 Hz, CHCH2), 3.64 (s, 3H, OCH3), 3.10 (dd, 1H, J=9.5 and 12.6 Hz, CHCH2), 2.65 (dd, 1H, J=3.8 and 12.6 Hz, CHCH2), 2.49 (s, 3H, ArCH3), 2.38 (s, 3H, ArCH3), 1.92 (s, 3H, ArCH3) ppm. MS 576.5 (M−).

Workup

  1. customthe progress of the reaction
  2. concentrationthe mixture was concentrated under reduced pressure on a rotary evaporator
  3. additionThe residue was treated with a solution 20% of KHSO4
  4. extractionextracted in EtOAc
  5. dry with materialThe EtOAc layer was dried over Na2SO4
  6. filtrationFiltration and removal of the solvent under reduced pressure
  7. customon a rotary evaporator

Sources & evidence

ORD record
ord-ecf34579f96548ed9e1796694406c588
Source dataset
uspto-grants-2005_05
Patent number
US06887877B2

Reaction notes

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