Lithium Hydroxide → HCID 22608523, compound

HRID 378148Notes

Reaction equation

[NH2:1][C:2]([NH:4][C:5]1[CH:6]=[C:7]([C:11]([NH:13][CH2:14][C:15]([NH:17][CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:19][C:20]([O:22]CC)=[O:21])=[O:16])=[O:12])[CH:8]=[CH:9][CH:10]=1)=[S:3].[OH-].[Li+].FC(F)(F)C(O)=O>O.C(#N)C>[NH2:1][C:2]([NH:4][C:5]1[CH:6]=[C:7]([C:11]([NH:13][CH2:14][C:15]([NH:17][CH:18]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:19][C:20]([OH:22])=[O:21])=[O:16])=[O:12])[CH:8]=[CH:9][CH:10]=1)=[S:3]

Participants

Conditions

Temperature: 25 °C

Procedure

The product of Example 116 (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-9aac8f09e9fc4430a4bb6d8f49476bd5
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06028223

Reaction notes

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