Diisopropylethylamine → HCID 58072043, compound

HRID 715708Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:22]=[C:21]3[C:16]([CH:17]=[CH:18][CH:19]=[N:20]3)=[C:15](OS(C(F)(F)F)(=O)=O)[N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[NH2:31][CH2:32][C@@H:33]1[O:37][C:36](=[O:38])[NH:35][CH2:34]1.C(N(C(C)C)CC)(C)C>CC(N(C)C)=O.ClCCl.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:22]=[C:21]3[C:16]([CH:17]=[CH:18][CH:19]=[N:20]3)=[C:15]([NH:31][CH2:32][C@@H:33]3[O:37][C:36](=[O:38])[NH:35][CH2:34]3)[N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 70 °C

Procedure

100 mg 6.1 and 70 mg of (S)-5-(aminomethyl)oxazolidine-2-one (2.19) (50%) were dissolved in dimethylacetamide. 0.175 mL (1.01 mmol) of diisopropylethylamine was added and the mixture was heated at 70° C. for 30 minutes and overnight at ambient temperature. The mixture was diluted with 20 mL dichloromethane and 20 mL water. The phases were separated and the water phase extracted with additional 10 mL dichloromethane. The combined organic phases were concentrated and the product purified via chromatography (SiO2: dichloromethane → dichloromethane/methanol 90:10). The product was recrystallized from ethyl acetate and methyl-tert-butylether.

Workup

customThe phases were separated
extractionthe water phase extracted with additional 10 mL dichloromethane
concentrationThe combined organic phases were concentrated
customthe product purified via chromatography (SiO2: dichloromethane → dichloromethane/methanol 90:10)
customThe product was recrystallized from ethyl acetate and methyl-tert-butylether

Sources & evidence

ORD record: ord-7934429cfe6143db8f9bedc1b3c441ee
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187478B2

Reaction notes

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