Water → HCID 58361501, compound

HRID 2076453Notes

Reaction equation

[C:1]1([S:7]([O:10][C:11]2[C:20]([Br:21])=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([CH:22]([OH:26])[CH2:23][CH:24]=C)=[N:18]3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C(C)=CC=CC=1C.[OH2:35].C(Cl)Cl>O1CCOCC1.O>[C:1]1([S:7]([O:10][C:11]2[C:20]([Br:21])=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([CH:22]([OH:26])[CH2:23][CH:24]=[O:35])=[N:18]3)=[CH:13][CH:12]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of compound 17 (330 mg, 0.760 mmol) in dioxane-water (3:1, 8 mL) were added 2,6-lutidine (0.177 mL, 1.73 mmol), K2OsO4·2 H2O (6 mg, 0.016 mmol), and NalO4 (655 mg, 3.06 mmol). The reaction was stirred at 25° C. and monitored by TLC. After the reaction was complete, water (10 mL) and CH2Cl2 (20 mL) were added. The organic layer was separated, and the aqueous layer was extracted by DCM (10 mL) three times. The organic layers were pooled, washed with brine, and dried over Na2SO4. The solvent was removed, and the product was purified with SiO2 column chromatography (hexanes/EtOAc=2/3) to afford aldehyde 18 (250 mg, 0.573 mmol, 75%) as a colorless oil. MS-ESI (m/z): [M+H]+ calculated for C18H15BrNO5S, 435.99 (79Br) and 437.98 (81Br); found 436.04 (79Br) and 437.97 (81Br).

Workup

customThe organic layer was separated
extractionthe aqueous layer was extracted by DCM (10 mL) three times
washwashed with brine
dry with materialdried over Na2SO4
customThe solvent was removed
customthe product was purified with SiO2 column chromatography (hexanes/EtOAc=2/3)

Sources & evidence

ORD record: ord-56373199af144c9cb5b3ed51cae5ab46
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923562B2

Reaction notes

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