Sodium Hydroxide → HCID 25183508, compound

HRID 1925742Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([S:13]([NH:16][C:17]2[CH:21]=[CH:20][S:19][C:18]=2[C:22]([O:24]C)=[O:23])(=[O:15])=[O:14])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1.[OH-].[Na+]>O1CCCC1.CO>[CH3:1][C:2]1[CH:3]=[C:4]([S:13]([NH:16][C:17]2[CH:21]=[CH:20][S:19][C:18]=2[C:22]([OH:24])=[O:23])(=[O:15])=[O:14])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 122 (85.0 mg; 0.22 mmol) in tetrahydrofuran (5 mL) and methanol (5 mL) was added aqueous sodium hydroxide (7.5 mL; 2N) and then heated at 80° C. for 16 hours. The reaction mixture was allowed to cool to room temperature and then extracted with diethyl ether. The aqueous layer was separated and acidified with aqueous hydrochloric acid (15 mL; 2N) then extracted with ethyl acetate (2×15 mL). The combined organic phases were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting crude residue was purified by automated silica gel column chromatography (Biotage®) eluting with dichloromethane/methanol to give the title product as an off-white solid (47 mg).

Workup

temperatureto cool to room temperature
extractionextracted with diethyl ether
customThe aqueous layer was separated
extractionthen extracted with ethyl acetate (2×15 mL)
dry with materialThe combined organic phases were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe resulting crude residue was purified by automated silica gel column chromatography (Biotage®)
washeluting with dichloromethane/methanol

Sources & evidence

ORD record: ord-b9002d043a9546818dc3c275d4fda78e
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178699B2

Reaction notes

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