1,1'-Carbonyldiimidazole → benzhydryl 1-[(Z)-[1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-oxo-2-[[(3S,4R)-2-oxo-4-[(2-oxoimidazolidin-1-yl)methyl]azetidin-3-yl]amino]ethylidene]amino]oxycyclopropane-1-carboxylate

HRID 708484Notes

Reaction equation

HRID 708484 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][C@@H:6]1[C@H:9]([NH:10][C:11](=[O:47])/[C:12](=[N:26]\[O:27][C:28]2([C:31]([O:33][CH:34]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:32])[CH2:30][CH2:29]2)/[C:13]2[N:14]=[C:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[S:16][CH:17]=2)[C:8](=[O:48])[NH:7]1.C1N=CN([C:54](N2C=NC=C2)=[O:55])C=1>C(Cl)(Cl)Cl>[C:22]([O:21][C:19]([NH:18][C:15]1[S:16][CH:17]=[C:13](/[C:12](=[N:26]/[O:27][C:28]2([C:31]([O:33][CH:34]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[O:32])[CH2:29][CH2:30]2)/[C:11](=[O:47])[NH:10][C@H:9]2[C@@H:6]([CH2:5][N:4]3[CH2:3][CH2:2][NH:1][C:54]3=[O:55])[NH:7][C:8]2=[O:48])[N:14]=1)=[O:20])([CH3:24])([CH3:23])[CH3:25]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 118379472benzhydryl 1-[(Z)-[2-[[(2R,3S)-2-[(2-aminoethylamino)methyl]-4-oxoazetidin-3-yl]amino]-1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-oxoethylidene]amino]oxycyclopropane-1-carboxylate

Product 1

HCID 118380235benzhydryl 1-[(Z)-[1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-oxo-2-[[(3S,4R)-2-oxo-4-[(2-oxoimidazolidin-1-yl)methyl]azetidin-3-yl]amino]ethylidene]amino]oxycyclopropane-1-carboxylateYield 49.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of benzhydryl 1-(((Z)-(2-(((2R,3S)-2-(((2-aminoethyl)amino)methyl)-4-oxoazetidin-3-yl)amino)-1-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-oxoethylidene)amino)oxy)cyclopropanecarboxylate (90 mg, 0.133 mmol) in chloroform (2.7 mL) was added CDI (43.1 mg, 0.266 mmol) and TEA (111 μl, 0.797 mmol). After 12 h, the reaction mixture was concentrated in vacuo. The crude residue was purified via silica gel chromatography (MeOH-DCM, 0-100%) to afford the title compound (46 mg, 49%). LCMS: Rt=0.95 min, m/z=704.0 (M+1), Method 2m_acidic.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe crude residue was purified via silica gel chromatography (MeOH-DCM, 0-100%)

Sources & evidence

ORD record
ord-27cc3506b2094d95aa07f5ff1d1e0285
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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