Hydrochloric Acid → HCID 69183660, compound

HRID 1394367Notes

Reaction equation

HRID 1394367 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([N:12]([CH2:21][CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][CH:27]([NH:30][C:31]3[CH:40]=[CH:39][C:34]([C:35]([O:37]C)=[O:36])=[CH:33][CH:32]=3)[CH2:26][CH2:25]2)[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[OH-].[Na+].Cl>C(O)C>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([N:12]([CH2:21][CH2:22][CH2:23][N:24]2[CH2:25][CH2:26][CH:27]([NH:30][C:31]3[CH:32]=[CH:33][C:34]([C:35]([OH:37])=[O:36])=[CH:39][CH:40]=3)[CH2:28][CH2:29]2)[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18538934HCID 18538934, compound

Product 1

HCID 69183660HCID 69183660, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of the compound obtained in Example 210 (51.8 mg, 0.09 mmol) in ethanol (2 mL) was added aqueous solution of 1N-sodium hydroxide (0.53 mL, 0.53 mmol), and the mixture was stirred at 90° C. for 5 hours. To the mixture was added dropwise aqueous solution of 1N-hydrochloric acid (0.53 mL, 0.53 mmol) under ice cooling, and the mixture was concentrated under reduced pressure. The concentrate was subjected to flash column chromatography (silica gel 5 g, ethyl acetate/methanol=1/0 to 1/1), and the desired fraction was concentrated under reduced pressure to give the titled compound (28 mg, 0.05 mmol, Yield 55%) as white amorphous substance.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. concentrationthe desired fraction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-45d5c2763d644ff79a8fd8a5f1d2de25
Source dataset
uspto-grants-2008_03
Patent number
US07348324B2

Reaction notes

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