Hydrochloric Acid → MK-5172

HRID 1008858Notes

Reaction equation

[C:1]([C@H:5]1[C:33](=[O:34])[N:32]2[CH2:35][C@@H:29]([CH2:30][C@H:31]2[C:36]([O:38]C)=[O:37])[O:28][C:17]2=[N:18][C:19]3[CH:20]=[C:21]([O:26][CH3:27])[CH:22]=[CH:23][C:24]=3[N:25]=[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[CH2:40][C@H:9]2[O:8][C:7](=[O:41])[NH:6]1)([CH3:4])([CH3:3])[CH3:2].O.C1COCC1.O[Li].O.Cl>CCOC(C)=O>[C:1]([C@H:5]1[C:33](=[O:34])[N:32]2[CH2:35][C@@H:29]([CH2:30][C@H:31]2[C:36]([OH:38])=[O:37])[O:28][C:17]2=[N:18][C:19]3[CH:20]=[C:21]([O:26][CH3:27])[CH:22]=[CH:23][C:24]=3[N:25]=[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[CH2:40][C@H:9]2[O:8][C:7](=[O:41])[NH:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 20 °C

Procedure

A solution (0.1 M) of methyl (1aR,5S,8S,10R,22aR)-5-tert-butyl-14-methoxy-3,6-dioxo-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradecahydro-8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoxaline-8-carboxylate in a 1:1 mixture of H2O/THF was treated with LiOH.H2O (3 eq). The resulting mixture was stirred at 20° C. for 18 h, acidified with aqueous HCl (0.2 M) and diluted with EtOAc. The organic phase was separated, washed with aqueous HCl (0.2 M) and brine then dried. Removal of the volatiles afforded the title compound (98%) as a solid. MS (ES+) m/z 555 (M+H)+

Workup

customThe organic phase was separated
washwashed with aqueous HCl (0.2 M) and brine
customthen dried
customRemoval of the volatiles

Sources & evidence

ORD record: ord-869e7aca686b4662936227130c76b8a9
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973040B2

Reaction notes

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