Dimethyl Sulfoxide → HCID 21907578, compound

HRID 1247475Notes

Reaction equation

CS(C)=O.C(Cl)(=O)C(Cl)=[O:7].[CH2:11]([C:13]1([CH2:28][CH2:29][OH:30])[C:18]2[NH:19][C:20]3[C:25]([C:17]=2[CH2:16][CH2:15][O:14]1)=[CH:24][CH:23]=[CH:22][C:21]=3[CH2:26][CH3:27])[CH3:12]>C(Cl)Cl.[NH4+].[Cl-]>[CH2:11]([C:13]1([CH2:28][CH:29]([OH:7])[OH:30])[C:18]2[NH:19][C:20]3[C:25]([C:17]=2[CH2:16][CH2:15][O:14]1)=[CH:24][CH:23]=[CH:22][C:21]=3[CH2:26][CH3:27])[CH3:12]

Participants

Conditions

Temperature: 0 °C

Procedure

Dry DMSO (71 μL, 1.0 mmol, 2.0 eq) was added dropwise to a solution of oxalyl chloride (66 μL, 0.75 mmol, 1.5 eq) in CH2Cl2 (1 mL) at −78° C. After stirring for ten minutes, a solution of compound 1 (136 μL, 0.5 mmol) in CH2Cl2 (4 mL) was added dropwise, and the reaction was stirred for an additional thirty minutes at −78° C. before the addition of TEA (2.79 μL, 2.0 mmol, 4.0 eq). The reaction mixture was then allowed to warm slowly to 0° C., diluted with saturated NH4Cl, and extracted twice with Et2O. The combined organic phases were washed with water and brine, dried with Na2SO4, concentrated, and purified by column chromatography using a gradient of 50:50:EtOAc:Hexane to 100% EtOAc to give a white solid (46 mg, 32%): mp 158–159° C. 1HNMR (CDCl3, δ TMS): 0.50 (t, 3H), 1.25 (t, 3H), 1.50 (m, 1H), 1.82 (m, 1H), 2.04 (m, 1H), 2.17 (m, 1H), 2.33 (m, 1H), 2.58 (q, 2H), 2.88 (m, 2H), 3.77 (m, 1H), 3.91 (m, 1H), 4.19 (q, 1H), 4.33 (m, 1H), 7.02–7.15 (m, 3H, Ar—H), 7.66 (br, 1H, NH). MS−: m/z 288 ([M−H]−). Anal. (C17H23NO3): C, H, N.

Workup

extractionextracted twice with Et2O
washThe combined organic phases were washed with water and brine
dry with materialdried with Na2SO4
concentrationconcentrated
custompurified by column chromatography

Sources & evidence

ORD record: ord-dde7028e261145d283f5407892736a64
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07129262B2

Reaction notes

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