Dimethyl Disulfide → HCID 71128808, compound

HRID 1468857Notes

Reaction equation

Br[C:2]1[CH:30]=[CH:29][C:5]([CH2:6][O:7][C@H:8]([C@@H:12]2[CH2:14][C@@H:13]2[CH:15]2[CH2:20][CH2:19][N:18]([C:21]3[N:26]=[CH:25][C:24]([CH2:27][CH3:28])=[CH:23][N:22]=3)[CH2:17][CH2:16]2)[CH2:9][O:10][CH3:11])=[CH:4][CH:3]=1.[Li]CCCC.[CH3:36][S:37]SC>C1COCC1>[CH2:27]([C:24]1[CH:23]=[N:22][C:21]([N:18]2[CH2:19][CH2:20][CH:15]([C@H:13]3[CH2:14][C@H:12]3[C@@H:8]([O:7][CH2:6][C:5]3[CH:29]=[CH:30][C:2]([S:37][CH3:36])=[CH:3][CH:4]=3)[CH2:9][O:10][CH3:11])[CH2:16][CH2:17]2)=[N:26][CH:25]=1)[CH3:28]

Participants

Conditions

Temperature: -78 °C

Procedure

To a cold (−78° C.), stirred solution of the product of step G (90 mg, 0.190 mmol) in THF (1.9 mL) was added n-BuLi (0.9 mL of 2.5 M solution in hexane, 0.228 mmol). After 10 min, dimethyldisulfide (23.2 mg, 0.247 mmol) was added and the mixture stirred for 45 min at −78° C. The reaction was quenched with a saturated aqueous solution of NH4Cl, and the aqueous layer was extracted with EtOAc (×3). The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated under vacuum to leave a residue which was purified by column chromatography on silica (elution with 5:1 hexane:ethyl acetate) to yield the title compound. MS (ESI) m/z 442 [M+H]+.

Workup

customThe reaction was quenched with a saturated aqueous solution of NH4Cl
extractionthe aqueous layer was extracted with EtOAc (×3)
dry with materialThe combined organic layers were dried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated under vacuum
customto leave a residue which
customwas purified by column chromatography on silica (elution with 5:1 hexane:ethyl acetate)

Sources & evidence

ORD record: ord-f4f5bd5a896f455eb869d6900545394c
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006228B2

Reaction notes

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