(Diethylamino)sulfur trifluoride → HCID 58247415, compound

HRID 2359659Notes

Reaction equation

C(N(S(F)(F)[F:7])CC)C.[C:10]([O:14][C:15]([N:17]1[CH2:21][CH2:20][CH2:19][C@H:18]1[CH2:22][NH:23][C:24]1[C:25]([O:36][C:37]2[CH:42]=[CH:41][C:40]([CH2:43]O)=[CH:39][CH:38]=2)=[N:26][C:27]([C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)=[N:28][CH:29]=1)=[O:16])([CH3:13])([CH3:12])[CH3:11]>C(Cl)Cl>[C:10]([O:14][C:15]([N:17]1[CH2:21][CH2:20][CH2:19][C@H:18]1[CH2:22][NH:23][C:24]1[C:25]([O:36][C:37]2[CH:42]=[CH:41][C:40]([CH2:43][F:7])=[CH:39][CH:38]=2)=[N:26][C:27]([C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)=[N:28][CH:29]=1)=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of (diethylamino)sulfur trifluoride (0.036 mL; 0.28 mmol) in CH2Cl2 (2 mL), cooled to −78° C., was added a solution of Compound 18b (100 mg; 0.21 mmol) in CH2Cl2 (1 mL). The reaction mixture was stirred at −78° C. for 20 min. The resultant mixture was partitioned between EtOAc and H2O. The organic phase was washed with water and dried over Na2SO4. The mixture was filtered and the solvent removed under reduced pressure to give the crude material. The crude material was purified by flash column chromatography (SiO2), eluting with a heptane-EtOAc gradient to afford Compound 18c (50 mg; 50% yield). MS: m/z 480.2 (M+H)+.

Workup

customThe resultant mixture was partitioned between EtOAc and H2O
washThe organic phase was washed with water
dry with materialdried over Na2SO4
filtrationThe mixture was filtered
customthe solvent removed under reduced pressure
customto give the crude material
customThe crude material was purified by flash column chromatography (SiO2)
washeluting with a heptane-EtOAc gradient

Sources & evidence

ORD record: ord-6c84b47b304a48129b56131513bc3770
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685990B2

Reaction notes

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