Lithium Hydroxide → (9R,11S,14S)-14-tert-butyl-13-oxo-8-oxa-12,15-diazatetracyclo[20.3.1.12,6.1 9,12]octacosa-1(26),2(28),3,5,22,24-hexaene-11-carboxylic acid

HRID 1879261Notes

Reaction equation

[Li+].[OH-].[C:3]([C@@H:7]1[NH:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][C:24]2[CH:32]=[C:20]([CH:21]=[CH:22][CH:23]=2)[C:19]2=[CH:33][C:15](=[CH:16][CH:17]=[CH:18]2)[CH2:14][O:13][C@H:12]2[CH2:34][N:9]([C@H:10]([C:35]([O:37]C)=[O:36])[CH2:11]2)[C:8]1=[O:39])([CH3:6])([CH3:5])[CH3:4]>C1COCC1.CCO.O>[C:3]([C@@H:7]1[NH:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][C:24]2[CH:32]=[C:20]([CH:21]=[CH:22][CH:23]=2)[C:19]2=[CH:33][C:15](=[CH:16][CH:17]=[CH:18]2)[CH2:14][O:13][C@H:12]2[CH2:34][N:9]([C@H:10]([C:35]([OH:37])=[O:36])[CH2:11]2)[C:8]1=[O:39])([CH3:6])([CH3:4])[CH3:5]

Participants

Conditions

Temperature: 40 °C

Procedure

LiOH (3.0 eq.) was added to a 0.05 M solution of methyl (9R,11S,14S)-14-tert-butyl-13-oxo-8-oxa-12,15-diazatetracyclo[20.3.1.12,6.1 9,12]octacosa-1(26),2(28),3,5,22,24-hexaene-11-carboxylate 104 in a mixture of THF:EtOH:H2O (2:1:1). The reaction mixture was stirred at 40° C. for 2 h then the solvent was evaporated under reduced pressure. Aqueous HCl (1N) was added to reach pH=6 and the mixture was evaporated to dryness to yield a dark solid which was used without further purification. MS (ES+) m/z 493 (M+H)+.

Workup

customthe solvent was evaporated under reduced pressure
additionAqueous HCl (1N) was added
customthe mixture was evaporated to dryness
customto yield a dark solid which
customwas used without further purification

Sources & evidence

ORD record: ord-f51d243a58e34598bf40da7545b86316
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314062B2

Reaction notes

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