Lithium Hydroxide → HCID 66842825, compound

HRID 1795469Notes

Reaction equation

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

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of the compound of Example 1 (207 mg) in THF/H2O (8 ml/2 ml) was added LiOH (30 mg) at 5° C. The mixture was stirred at 5° C. for 20 hours, quenched with 6N HCl (1 ml) and extracted with AcOEt. The organic layer was washed with H2O and brine, dried (MgSO4) and evaporated. The residue was recrystallized from a mixture of MeOH, diethyl ether and hexane to yield the title compound (147 mg). The compound of Example 2 (301 mg) was also hydrolyzed in a similar manner to give the title compound (238 mg) mp. 196-198° C.; IR (Nujol) 3300, 3270, 1705, 1651, 1462, 1126 cm−1; MS (ESI−Q1MS) m/z 530 (M−H).

Workup

customquenched with 6N HCl (1 ml)
extractionextracted with AcOEt
washThe organic layer was washed with H2O and brine
dry with materialdried (MgSO4)
customevaporated
customThe residue was recrystallized from a mixture of MeOH, diethyl ether and hexane

Sources & evidence

ORD record: ord-53a468125151466ea3425a0d8f8972c1
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07026501B2

Reaction notes

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