Hydrochloric Acid → HCID 45492946, compound

HRID 252831Notes

Reaction equation

HRID 252831 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([NH:10][C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17]CC)=[O:16])=[CH:13][CH:12]=2)=[O:9])[CH2:4][CH2:3]1.O[Li].O.C1COCC1.Cl>O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([NH:10][C:11]2[CH:21]=[CH:20][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=2)=[O:9])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 59736745HCID 59736745, compound

Product 1

HCID 45492946HCID 45492946, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 162 (1.39 g, 4.77 mmol) and LiOH.H2O (300 mg, 7.16 mmol) in 1:1 THF:water (8 ml) was stirred at room temperature for 24 h. 1 M HCl was added to reach pH=5 and the solvent was evaporated. The title compound was purified by preparative HPLC (Aquasil C18, reverse phase, eluent: MeOH/water) to give 979 mg (78%) of the title compound 163 as a white powder. 1H NMR: (400 MHz, DMSO) δ (ppm): 8.81 (s, 1H), 7.78 (dt, J=8.6, 1.8 Hz, 2H), 7.53 (dt, J=8.8, 2.0 Hz, 2H), 3.44 (t, J=4.9 Hz, 4H), 2.31 (t, J=5.0 Hz, 4H), 2.19 (s, 3H).

Workup

  1. customthe solvent was evaporated
  2. customThe title compound was purified by preparative HPLC (Aquasil C18, reverse phase, eluent: MeOH/water)

Sources & evidence

ORD record
ord-d37aa13ea6834069b22cb0386a4408b8
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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