Lithium Hydroxide → 3-[1-(3-tert-Butoxycarbonylamino-propyl)-piperidin-4-yl]-2-oxo-2,9-dihydro-3H-10-oxa-1,3,9-triaza-anthracene-7-carboxylic acid

HRID 570159Notes

Reaction equation

[Li+].[OH-].C[O:4][C:5]([C:7]1[CH:20]=[C:19]2[C:10]([O:11][C:12]3[CH:17]([NH:18]2)[NH:16][C:15](=[O:21])[N:14]([CH:22]2[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:24][CH2:23]2)[CH:13]=3)=[CH:9][CH:8]=1)=[O:6]>C1COCC1>[C:35]([O:34][C:32]([NH:31][CH2:30][CH2:29][CH2:28][N:25]1[CH2:24][CH2:23][CH:22]([N:14]2[CH:13]=[C:12]3[C:17]([NH:18][C:19]4[C:10]([O:11]3)=[CH:9][CH:8]=[C:7]([C:5]([OH:6])=[O:4])[CH:20]=4)=[N:16][C:15]2=[O:21])[CH2:27][CH2:26]1)=[O:33])([CH3:38])([CH3:36])[CH3:37]

Participants

Conditions

Temperature: 50 °C

Procedure

1M of LiOH aqueous solution (4.5 mL, 3 equiv) and 3-[1-(3-tert-Butoxycarbonylamino-propyl)-piperidin-4-yl]-2-oxo-2,3,9,9a-tetrahydro-1H-10-oxa-1,3,9-triaza-anthracene-7-carboxylic acid methyl ester (5, 760 mg, 1.52 mmol, 1.0 equiv) was added to THF (5 mL), warmed up to 50° C. and stirred until LCMS showed no starting material left. The reaction solution was cooled to RT and extracted with EtOAc. The aqueous layer was acidified to pH 2 and the desired product was precipitated and filtered to yield 3-[1-(3-tert-Butoxycarbonylamino-propyl)-piperidin-4-yl]-2-oxo-2,9-dihydro-3H-10-oxa-1,3,9-triaza-anthracene-7-carboxylic acid (412 mg, 738 mg theoretical, 56%) as a light brown solid. For 6: C24H31N5O6, LCMS (EI) m/e 486(M++H).

Workup

waitleft
temperatureThe reaction solution was cooled to RT
extractionextracted with EtOAc
customthe desired product was precipitated
filtrationfiltered

Sources & evidence

ORD record: ord-6a778ac198034c638c9e0eb4f50d9896
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023843B2

Reaction notes

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