Hydrochloric Acid → HCID 69155979, compound

HRID 750351Notes

Reaction equation

HRID 750351 reaction equation
C[O:2][C:3](=[O:38])[CH2:4][NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:25]([C:26](=[O:29])[CH2:27][CH3:28])=[C:24]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([Br:36])[CH:22]=3)[C:17]2=[O:37])=[CH:11][CH:10]=1)(=[O:8])=[O:7].CO.[OH-].[Na+].Cl>C1COCC1>[Br:36][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][CH:20]=1)[C:17](=[O:37])[N:16]([CH2:15][C:12]1[CH:13]=[CH:14][C:9]([S:6]([NH:5][CH2:4][C:3]([OH:38])=[O:2])(=[O:8])=[O:7])=[CH:10][CH:11]=1)[C:25]([C:26](=[O:29])[CH2:27][CH3:28])=[C:24]2[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 69156791HCID 69156791, compound

Product 1

HCID 69155979HCID 69155979, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of [4-(6-bromo-1-oxo-4-phenyl-3-propionyl-1H-isoquinolin-2-ylmethyl)benzenesulfonylamino]acetic acid methyl ester (70 mg), methanol (2.0 ml) and THF (2.0 ml) was added 1N sodium hydroxide (0.23 ml) at room temperature with stirring, and the mixture was stirred at the same temperature for 18 hrs. The reaction mixture was neutralized with 1N hydrochloric acid and concentrated under reduced pressure. The residue was purified by preparative HPLC to give the title compound (33 mg) in beige crystals. 1H NMR (CDCl3) δ: 0.52 (3H, t, J=6.9 Hz), 1.78 (2H, q, J=6.9 Hz), 3.82 (2H, d, J=6.0 Hz), 5.25-5.36 (3H, m), 7.23-7.31 (2H, m), 7.33 (2H, d, J=8.4 Hz), 7.44-7.55 (4H, m), 7.70 (1H, dd, J=1.8, 8.4 Hz), 7.80 (2H, d, J=8.4 Hz), 8.37 (1H, d, J=8.4 Hz). HPLC analysis: purity 95.2% (retention time: 4.38 min). MS (ESI+): 583 (M+H), 585.

Workup

  1. stirringthe mixture was stirred at the same temperature for 18 hrs
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-c1e1fc9b412a489783e0b981a518f2f7
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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