Hydrochloric Acid → 2-{4'-[(4-benzyloxy-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonyl}-L-valine

HRID 29277Notes

Reaction equation

HRID 29277 reaction equation
C[O:2][C:3](=[O:44])[C@:4]([S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]3[O:28][C:29]4[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH2:37][C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)[C:30]=4[CH:31]=3)=[O:26])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)(=[O:11])=[O:10])([CH:6]([CH3:8])[CH3:7])[NH2:5].[Li+].[OH-].O.Cl>C1COCC1.CO.C(OCC)(=O)C>[CH2:37]([O:36][C:32]1[C:30]2[CH:31]=[C:27]([C:25]([NH:24][C:21]3[CH:22]=[CH:23][C:18]([C:15]4[CH:16]=[CH:17][C:12]([S:9]([C@@:4]([C:3]([OH:44])=[O:2])([CH:6]([CH3:8])[CH3:7])[NH2:5])(=[O:11])=[O:10])=[CH:13][CH:14]=4)=[CH:19][CH:20]=3)=[O:26])[O:28][C:29]=2[CH:35]=[CH:34][CH:33]=1)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 68713607HCID 68713607, compound

Product 1

HCID 687151062-{4'-[(4-benzyloxy-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonyl}-L-valineYield 38.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-{4′-[(4-Benzyloxy-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonyl}-L-valine methyl ester (0.24 mmol) was dissolved in THF and MeOH (2:1) (0.6 mL). A 5 M solution of LiOH in water (5.0 equiv.) was then added. The reaction was stirred at room temperature overnight. The reaction was diluted with ethyl acetate and acidified with 1N hydrochloric acid. The organic layer was washed with brine (2×), dried (magnesium sulfate), filtered and concentrated to afford 55 mg of the pure 2-{4′-[(4-benzyloxy-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonyl}-L-valine. LCMS MH+ (m/z) 599. 1H NMR (300 MHz, DMSO-d6): δ 10.55 ppm (s, 1H), 8.08 ppm (d, 1H, J=9.2 Hz), 7.97-7.76 ppm (m, 8 H), 7.58-7.28 ppm (m, 7H), 7.02 ppm (d, 1H, J=8.0 Hz), 5.31 ppm (s, 2H), 3.94 ppm (s, 2H), 3.58-3.52 ppm (m, 1H), 1.96-1.90 ppm (m, 1H), 0.84 ppm (d, 3H, J=7.0 Hz), 0.81 ppm (d, 3H, J=7.0 Hz).

Workup

  1. washThe organic layer was washed with brine (2×)
  2. dry with materialdried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4c3ac635ae1b48e3891d899061231ab2
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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