Lithium Hydroxide → HCID 131721679, compound

HRID 378146Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]([NH:21][C:22]2[CH:23]=[C:24]([C:28]([NH:30][CH2:31][C:32]([NH:34][CH:35]([C:42]3[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=3)[CH2:36][C:37]([O:39]CC)=[O:38])=[O:33])=[O:29])[CH:25]=[CH:26][CH:27]=2)=[O:20])(=[O:17])=[O:16])=[CH:11][CH:10]=1.[OH-].[Li+].FC(F)(F)C(O)=O>O.C(#N)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][C:9]1[CH:10]=[CH:11][C:12]([S:15]([NH:18][C:19]([NH:21][C:22]2[CH:23]=[C:24]([C:28]([NH:30][CH2:31][C:32]([NH:34][CH:35]([C:42]3[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=3)[CH2:36][C:37]([OH:39])=[O:38])=[O:33])=[O:29])[CH:25]=[CH:26][CH:27]=2)=[O:20])(=[O:16])=[O:17])=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 25 °C

Procedure

The compound of Example 111 (500 mg, 0.095 mmol) was dissolved in water/acetonitrile (1:1), followed by the addition of lithium hydroxide (100 mg, 0.4 mmol). The reaction mixture was stirred at 25° C., and monitored by HPLC. After complete hydrolysis (1-2 hours) trifluoroacetic acid was added until pH=2. The product was purified by reverse phase chromatography (water/acetonitrile) and lyophilized to result in a white solid (350 mg). MS and 1H-NMR were consistent with the proposed structure.

Workup

additionwas added until pH=2
customThe product was purified by reverse phase chromatography (water/acetonitrile)

Sources & evidence

ORD record: ord-b3c5638b56164ab38a7229492ee69c7b
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06028223

Reaction notes

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