Hydrochloric Acid → HCID 18538868, compound

HRID 1394368Notes

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]([CH2:30][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.ClCCl.CO>C(O)C>[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([C:10]([N:12]([CH2:21][CH2:22][CH2:23][N:24]2[CH2:25][CH2:26][CH:27]([CH2:30][C:31]3[CH:40]=[CH:39][C:34]([C:35]([OH:37])=[O:36])=[CH:33][CH:32]=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])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of the compound obtained in Example 233 (200 mg, 0.37 mmol) in ethanol (2 mL) was added aqueous solution of 1N-sodium hydroxide (0.56 mL, 0.56 mmol), and the mixture was stirred at 80° C. for 3 hours. To the mixture was added, dropwise aqueous solution of 1N-hydrochloric acid (0.56 mL, 0.56 mmol) under ice cooling, and the mixture was concentrated under reduced pressure. The concentrate was subjected to flash column chromatography (silica gel 20 g, dichloromethane/methanol=20/1 to 2/1), and the desired fraction was concentrated under reduced pressure. To the concentrate was added diisoprpyl ether, and the resulting precipitates were collected by filtration to give the titled compound (120 mg, 0.21 mmol, Yield 56%) as white amorphous substance.

Workup

additionTo the mixture was added
concentrationthe desired fraction was concentrated under reduced pressure
additionTo the concentrate was added diisoprpyl ether
customthe resulting precipitates
filtrationwere collected by filtration

Sources & evidence

ORD record: ord-82959ddce314495faa43766f5712a0e3
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07348324B2

Reaction notes

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