Hydrogen Peroxide → HCID 70872163, compound

HRID 1475703Notes

Reaction equation

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

Participants

Conditions

Temperature: -25 °C

Procedure

The compound of step 1 of example 56 (500 mg, 1.14 mmol) was dissolved in THF (5 ml) and cooled to −25° C. Borane-tetrahydrofuran complex (2.29 ml of a 1 M solution in THF, 2.29 mmol) was added and the mixture was kept overnight at 0° C. Hydrogen peroxide (2.5 ml, 30% in water) and sodium hydroxide (2.5 ml, 20% in water) were added sequentially and stirring was continued at room temperature. The mixture was partitioned between water and EA, the aqueous phase extracted with EA, and the combined organic phases were dried over sodium sulfate and evaporated to dryness. The residue was purified by silica gel chromatography (HEP/EA gradient) to yield the title compound.

Workup

customwas continued at room temperature
customThe mixture was partitioned between water and EA
extractionthe aqueous phase extracted with EA
dry with materialthe combined organic phases were dried over sodium sulfate
customevaporated to dryness
customThe residue was purified by silica gel chromatography (HEP/EA gradient)

Sources & evidence

ORD record: ord-e06268b2ebe64a10a217a7793570054f
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018383B2

Reaction notes

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