Diisopropylethylamine → HCID 178454253, compound

HRID 708497Notes

Reaction equation

FC(F)(F)C(O)=O.[NH2:8][CH2:9][C:10]1[CH:14]=[N:13][N:12]([CH2:15][C@@H:16]2[C@H:19]([NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18](=[O:31])[NH:17]2)[N:11]=1.CCN(C(C)C)C(C)C.[C:41]([O:45][C:46]([N:48]([CH2:63][CH:64]1[CH2:67][N:66]([C:68]([O:70][C:71]([CH3:74])([CH3:73])[CH3:72])=[O:69])[CH2:65]1)[C:49](N1C=CC=N1)=[N:50][C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])=[O:47])([CH3:44])([CH3:43])[CH3:42]>O1CCOCC1>[CH2:23]([O:22][C:21]([NH:20][C@@H:19]1[C:18](=[O:31])[NH:17][C@@H:16]1[CH2:15][N:12]1[N:11]=[C:10]([CH2:9][NH:8][C:49](=[N:50][C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[N:48]([CH2:63][CH:64]2[CH2:65][N:66]([C:68]([O:70][C:71]([CH3:72])([CH3:74])[CH3:73])=[O:69])[CH2:67]2)[C:46]([O:45][C:41]([CH3:44])([CH3:42])[CH3:43])=[O:47])[CH:14]=[N:13]1)=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of benzyl ((2R,3S)-2-((4-(aminomethyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidin-3-yl)carbamate 2,2,2-trifluoroacetate (340 mg, 0.77 mmol) in dioxane (6 mL) was added DIPEA (0.147 mL, 0.842 mmol) and a solution of tert-butyl 3-((N,N′-bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboximidamido)methyl)azetidine-1-carboxylate (367 mg, 0.765 mmol) in dioxane (1 mL). After heating to 60° C. for 12 h, the reaction mixture was concentrated in vacuo and purified via silica gel chromatography (EtOAc-heptane, 0-95%) to afford the title compound (390 mg, 69%). LCMS: Rt=0.94 min, m/z=742.5 (M+1) Method 2m_acidic.

Workup

concentrationthe reaction mixture was concentrated in vacuo
custompurified via silica gel chromatography (EtOAc-heptane, 0-95%)

Sources & evidence

ORD record: ord-3a9a599895ac404d82ddae194bb923ce
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174978B2

Reaction notes

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