Hydrochloric Acid → HCID 10279035, compound

HRID 2116611Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of example 34 (800 mg, 1.5 mmol) in THF/Ethanol (5/20 mL) was added 1N NaOH (10 mmol, 10 mL). The resulting mixture was stirred at 50° C. for 2 hours, and after cooling at room temperature 1N HCl (10 mmol, 10 mL) was added. The resulting mixture was concentrated in vacuo, then the residue was flash chromatographed CH2Cl2/MeOH (98:2) to give the title compound (310 mg, 0.61 mmol) in a 40% yield as a colorless oil.

Workup

additionwas added
concentrationThe resulting mixture was concentrated in vacuo
customchromatographed CH2Cl2/MeOH (98:2)

Sources & evidence

ORD record: ord-69240f31d2124651aafb075e3fd0df65
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07439259B2

Reaction notes

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