Dimethylformamide → HCID 178453513, compound

HRID 708491Notes

Reaction equation

[NH:1]=[C:2]([NH:5][CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])SC.C(N(CC)CC)C.[NH2:24][CH2:25][C:26]1[CH:30]=[N:29][N:28]([CH2:31][C@@H:32]2[C@H:35]([NH:36][C:37](=[O:53])/[C:38](=[N:45]\[O:46][C:47]3([C:50]([OH:52])=[O:51])[CH2:49][CH2:48]3)/[C:39]3[N:40]=[C:41]([NH2:44])[S:42][CH:43]=3)[C:34](=[O:54])[N:33]2[S:55]([OH:58])(=[O:57])=[O:56])[N:27]=1.CN(C=O)C>O1CCOCC1.CCOC(C)=O.O>[NH2:44][C:41]1[S:42][CH:43]=[C:39](/[C:38](=[N:45]/[O:46][C:47]2([C:50]([OH:52])=[O:51])[CH2:49][CH2:48]2)/[C:37]([NH:36][C@@H:35]2[C:34](=[O:54])[N:33]([S:55]([OH:58])(=[O:56])=[O:57])[C@@H:32]2[CH2:31][N:28]2[N:27]=[C:26]([CH2:25][NH:24][C:2](=[NH:1])[NH:5][CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH:30]=[N:29]2)=[O:53])[N:40]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of tert-butyl (3-((imino(methylthio)methyl)amino)propyl)carbamate (32.1 mg, 87 μmol) in dioxane (1 mL, ratio: 2) at rt was added triethylamine (30 μL, 0.22 mmol), 1-(((Z)-(2-(((2R,3S)-2-((4-(aminomethyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxo-1-sulfoazetidin-3-yl)amino)-1-(2-aminothiazol-4-yl)-2-oxoethylidene)amino)oxy)cyclopropanecarboxylic acid (example 19, 23 mg, 43 μmol), and DMF (0.5 mL, ratio: 1). After heated to 60° C. for 17 h, the reaction mixture was diluted with EtOAc and water. The aqueous layer was separated, concentrated in vacuo, azeotroped with toluene, and dried on high vac to give the title compound (assumed quantitative). LCMS: Rt=0.51 min, m/z=729.6 (M+1), Method 2m_acidic.

Workup

customThe aqueous layer was separated
concentrationconcentrated in vacuo
customazeotroped with toluene
customdried on high vac

Sources & evidence

ORD record: ord-aac4f9ca47f74d2e800c4d468a2a3e0c
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174978B2

Reaction notes

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