Hydrochloric Acid → HCID 68956421, compound

HRID 2067725Notes

Reaction equation

O1CCCC1.[NH:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH2:11][CH:12]([CH2:43][C:44]1[NH:45][CH:46]=[CH:47][N:48]=1)[CH2:13][NH:14][C:15]([C:17]1[CH:42]=[CH:41][C:20]([CH2:21][N:22]2[CH:26]([C:27]([O:29]CC)=[O:28])[CH2:25][C:24]3([CH2:36][CH2:35][N:34]([CH2:37][CH:38]([CH3:40])[CH3:39])[CH2:33][CH2:32]3)[CH2:23]2)=[CH:19][CH:18]=1)=[O:16].[OH-].[Na+].Cl>CO>[NH:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH2:11][CH:12]([CH2:43][C:44]1[NH:45][CH:46]=[CH:47][N:48]=1)[CH2:13][NH:14][C:15]([C:17]1[CH:18]=[CH:19][C:20]([CH2:21][N:22]2[CH:26]([C:27]([OH:29])=[O:28])[CH2:25][C:24]3([CH2:32][CH2:33][N:34]([CH2:37][CH:38]([CH3:39])[CH3:40])[CH2:35][CH2:36]3)[CH2:23]2)=[CH:41][CH:42]=1)=[O:16]

Participants

Conditions

Temperature: 50 °C

Procedure

To a tetrahydrofuran (2 mL)-methanol (2 mL) solution of the compound (51 mg) produced in Example 80(3), an aqueous 2N sodium hydroxide solution (0.5 mL) was added. The reaction solution was stirred at 50° C. for 3 hours. To the reaction solution, 1N hydrochloric acid was added so as to adjust the pH to about 5. The reaction solution was concentrated under reduced pressure. The residue was washed with ethanol. An insoluble salt was removed by filtration, and then the filtrate was concentrated. The residue was purified by silica gel chromatography (dichloromethane:methanol: 28% aqueous ammonia=8:2:0.5) to obtain the title compound (35 mg) having the following physical properties.

Workup

concentrationThe reaction solution was concentrated under reduced pressure
washThe residue was washed with ethanol
customAn insoluble salt was removed by filtration
concentrationthe filtrate was concentrated
customThe residue was purified by silica gel chromatography (dichloromethane:methanol: 28% aqueous ammonia=8:2:0.5)

Sources & evidence

ORD record: ord-a1bcbfea0ef844f0ac57dbfbf0604e3a
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293896B2

Reaction notes

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