Hydrochloric Acid → HCID 86643489, compound

HRID 1423377Notes

Reaction equation

[CH:1]1([C@@H:7]2[NH:32][C:31](=[O:33])[O:30][CH2:29][C:28]([CH3:35])([CH3:34])[CH2:27][CH2:26][CH2:25][C:24]3[CH:36]=[C:37]4[C:21](=[CH:22][C:23]=3[O:38][CH3:39])[N:20]3[C:16](=[N:17][CH:18]=[CH:19]3)[CH:15]=[C:14]4[O:13][C@H:12]3[CH2:40][N:9]([C@H:10]([C:41]([O:43]C)=[O:42])[CH2:11]3)[C:8]2=[O:45])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].[OH-].Cl>C1COCC1.CO.O>[CH:1]1([C@@H:7]2[NH:32][C:31](=[O:33])[O:30][CH2:29][C:28]([CH3:35])([CH3:34])[CH2:27][CH2:26][CH2:25][C:24]3[CH:36]=[C:37]4[C:21](=[CH:22][C:23]=3[O:38][CH3:39])[N:20]3[C:16](=[N:17][CH:18]=[CH:19]3)[CH:15]=[C:14]4[O:13][C@H:12]3[CH2:40][N:9]([C@H:10]([C:41]([OH:43])=[O:42])[CH2:11]3)[C:8]2=[O:45])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of the product from Step 9, methyl (3R,5S,8S)-8-cyclohexyl-18-methoxy-13,13-dimethyl-7,10-dioxo-2,11-dioxa-6,9,21,24-tetraazapentacyclo[15.9.2.13,6.020,27.021,25]nonacosa-1(26),17,19,22,24,27-hexaene-5-carboxylate (100 mg, 0.161 mmol) in THF (4 mL), MeOH (1 mL) and water (1 mL) was added LiOH (39 mg, 1.61 mmol). The mixture was then heated to 50° C. for 1 h and 1N HCl was then added to neutralize the base. The mixture was then extracted with EtOAc, the organic layer was dried over MgSO4, and the solvent was removed in vacuo to yield the title compound. LRMS (M+H)+=607.1.

Workup

extractionThe mixture was then extracted with EtOAc
dry with materialthe organic layer was dried over MgSO4
customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-c977010d88e645f7899bad87c2bb0271
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927569B2

Reaction notes

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