Hydrochloric Acid → HCID 178440311, compound

HRID 1625219Notes

Reaction equation

Cl.[OH:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10]2[CH:18]=[C:17]([N:19]3[C:23]4=[N:24][CH:25]=[CH:26][C:27]([C:28]5[CH:29]=[C:30]6[CH:36]=[CH:35][N:34](COCC[Si](C)(C)C)[C:31]6=[N:32][CH:33]=5)=[C:22]4[C:21]([CH:45]([CH3:47])[CH3:46])=[N:20]3)[CH:16]=[CH:15][C:11]=2[C:12]([NH2:14])=[O:13])[CH2:5][CH2:4]1.[OH-].[Na+]>O.C1COCC1>[OH:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([NH:9][C:10]2[CH:18]=[C:17]([N:19]3[C:23]4=[N:24][CH:25]=[CH:26][C:27]([C:28]5[CH:29]=[C:30]6[CH:36]=[CH:35][NH:34][C:31]6=[N:32][CH:33]=5)=[C:22]4[C:21]([CH:45]([CH3:47])[CH3:46])=[N:20]3)[CH:16]=[CH:15][C:11]=2[C:12]([NH2:14])=[O:13])[CH2:7][CH2:8]1

Participants

Conditions

Temperature: 50 °C

Procedure

Hydrochloric acid (a 6.0 M solution in water, 0.78 mL) was added to a solution of compound (13b) (0.100 g) in THF (0.78 mL), followed by stirring at 50° C. for 12 hr. The pH was adjusted to 10 with an aqueous sodium hydroxide solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline. The organic layer after the washing was dried over anhydrous sodium sulfate, and then the solvent was distilled away. Chloroform and ether were added to the residue, and the precipitate was collected by filtration to obtain compound (13) (0.057 g, 71%) as a white solid.

Workup

extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with saturated saline
dry with materialThe organic layer after the washing was dried over anhydrous sodium sulfate
distillationthe solvent was distilled away
additionChloroform and ether were added to the residue
filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record: ord-f661756094584920b344e0ca0d8d44cc
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08779142B2

Reaction notes

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