Lithium Hydroxide → (9R,11S,14S,20E)-14-cyclohexyl-13-oxo-8-oxa-12,15-diazatetracyclo[20.3.1.12,6.19,12]octacosa-1(26),2(28),3,5,20,22,24-heptaene-11-carboxylic acid

HRID 1879267Notes

Reaction equation

[Li+].[OH-].[CH:3]1([C@@H:9]2[NH:33][CH2:32][CH2:31][CH2:30][CH2:29][CH:28]=[CH:27][C:26]3[CH:34]=[C:22]([CH:23]=[CH:24][CH:25]=3)[C:21]3=[CH:35][C:17](=[CH:18][CH:19]=[CH:20]3)[CH2:16][O:15][C@H:14]3[CH2:36][N:11]([C@H:12]([C:37]([O:39]C)=[O:38])[CH2:13]3)[C:10]2=[O:41])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1>C1COCC1.CCO.O>[CH:3]1([C@@H:9]2[NH:33][CH2:32][CH2:31][CH2:30][CH2:29][CH:28]=[CH:27][C:26]3[CH:34]=[C:22]([CH:23]=[CH:24][CH:25]=3)[C:21]3=[CH:35][C:17](=[CH:18][CH:19]=[CH:20]3)[CH2:16][O:15][C@H:14]3[CH2:36][N:11]([C@H:12]([C:37]([OH:39])=[O:38])[CH2:13]3)[C:10]2=[O:41])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

Conditions

Temperature: 40 °C

Procedure

LiOH (3.0 eq.) was added to a 0.04M solution of methyl (9R,11S,14S,20E)-14-cyclohexyl-13-oxo-8-oxa-12,15-diazatetracyclo[20.3.1.12,6.19,12]octacosa-1(26),2(28),3,5,20,22,24-heptaene-11-carboxylate 110 in a mixture of THF:EtOH:H2O (2:1:1) and the reaction mixture was stirred at 40° C. for 2 h. The solvents were removed under reduced pressure, the residue was suspended in EtOAc/H2O, aqueous (1N) HCl was added to acidic pH and the phases separated. The collected organic layers were dried (Na2SO4) and evaporated under reduced pressure to afford a residue which was used without further purification. MS (ES+) m/z 517 (M+H)+

Workup

customThe solvents were removed under reduced pressure
additionaqueous (1N) HCl was added to acidic pH
customthe phases separated
dry with materialThe collected organic layers were dried (Na2SO4)
customevaporated under reduced pressure
customto afford a residue which
customwas used without further purification

Sources & evidence

ORD record: ord-0a3401424a61463ebcf42a1c5d6ced61
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314062B2

Reaction notes

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