1,1'-Carbonyldiimidazole → HCID 118379510, compound

HRID 708447Notes

Reaction equation

HRID 708447 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([OH:48])[CH2:11][NH:12][CH2:13][C@@H:14]1[C@H:17]([NH:18][C:19](=[O:46])/[C:20](=[N:34]\[O:35][C:36]([CH3:45])([CH3:44])[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])/[C:21]2[N:22]=[C:23]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[S:24][CH:25]=2)[C:16](=[O:47])[NH:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N=CN([C:54](N2C=NC=C2)=[O:55])C=1>C(Cl)Cl>[CH2:1]([O:8][CH2:9][C@@H:10]1[O:48][C:54](=[O:55])[N:12]([CH2:13][C@@H:14]2[C@H:17]([NH:18][C:19](=[O:46])/[C:20](=[N:34]\[O:35][C:36]([CH3:45])([CH3:44])[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])/[C:21]3[N:22]=[C:23]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[S:24][CH:25]=3)[C:16](=[O:47])[NH:15]2)[CH2:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 118379647HCID 118379647, compound

Product 1

HCID 118379510HCID 118379510, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared in analogous manner to example 63 step 2, using tert-butyl 2-(((Z)-(2-(((2R,3S)-2-((((R)-3-(benzyloxy)-2-hydroxypropyl)amino)methyl)-4-oxoazetidin-3-yl)amino)-1-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-oxoethylidene)amino)oxy)-2-methylpropanoate (126 mg, 0.182 mmol), CDI (53 mg, 0.33 mmol), DCM (5 mL). The crude residue was purified via silica gel chromatography (MeOH-DCM, 3-5%) to afford the title compound (76 mg, 58%). LCMS: m/z=715.3 (M−1).

Workup

  1. customPrepared in analogous manner to example 63 step 2
  2. customThe crude residue was purified via silica gel chromatography (MeOH-DCM, 3-5%)

Sources & evidence

ORD record
ord-9511a940a6b14a1d9bbb0cb33db30737
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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