1,1'-Carbonyldiimidazole → HCID 140689333, compound

HRID 708389Notes

Reaction equation

HRID 708389 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:29]/[O:30][C:31]([CH3:40])([CH3:39])[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])/[C:15]([NH:17][C@@H:18]2[C:21](=[O:22])[NH:20][C@@H:19]2[CH2:23][NH:24][CH2:25][C@H:26]([OH:28])[CH3:27])=[O:16])[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1N=CN([C:46](N2C=NC=C2)=[O:47])C=1>C(Cl)(Cl)Cl.CCOC(C)=O.O>[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:29]/[O:30][C:31]([CH3:39])([CH3:40])[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])/[C:15]([NH:17][C@@H:18]2[C:21](=[O:22])[NH:20][C@@H:19]2[CH2:23][N:24]2[CH2:25][C@@H:26]([CH3:27])[O:28][C:46]2=[O:47])=[O:16])[N:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 118380226HCID 118380226, compound

Product 1

HCID 140689333HCID 140689333, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 22728543Water ethylacetateSolvent

Procedure

To a solution of tert-butyl 2-(((Z)-(1-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-(((2R,3S)-2-((((R)-2-hydroxypropyl)amino)methyl)-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoate (185 mg, 0.316 mmol) in chloroform (3.16 mL) was added CDI (257 mg, 1.58 mmol). After stirring at rt for 20 min the solution was diluted with EtOAc/water and the layers separated. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4 and concentrated in vacuo. The crude residue was purified via silica gel chromatography (Acetone-DCM, 0-100%) to afford the title compound (81 mg, 42%). LCMS: Rt=0.92 min, m/z=611.2 (M+1) Method 2m_acidic.

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted with EtOAc
  3. dry with materialthe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified via silica gel chromatography (Acetone-DCM, 0-100%)

Sources & evidence

ORD record
ord-d023e01b64a548d2947727c862243d4e
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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