1,1'-Carbonyldiimidazole → HCID 140689319, compound

HRID 708437Notes

Reaction equation

HRID 708437 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:38]/[O:39][C:40]([CH3:49])([CH3:48])[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])/[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:37])[CH2:27][O:28][CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])=[O:16])[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1N=CN([C:55](N2C=NC=C2)=[O:56])C=1>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:38]/[O:39][C:40]([CH3:49])([CH3:48])[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])/[C:15](=[O:16])[NH:17][C@H:18]2[C@@H:19]([CH2:23][N:24]3[CH2:25][C@@H:26]([CH2:27][O:28][CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:34])([CH3:36])[CH3:35])[O:37][C:55]3=[O:56])[NH:20][C:21]2=[O:22])[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 140689347HCID 140689347, compound

Product 1

HCID 140689319HCID 140689319, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(((Z)-(1-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-(((2R,3S)-2-((S)-9-hydroxy-2,2-dimethyl-5,7-dioxa-11-aza-2-siladodecan-12-yl)-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoate (155 mg, 0.21 mmol) in DCM (10 mL) at 0° C. was added CDI (62 mg, 0.38 mmol). After stirring at <15° C. for 2 h, the reaction mixture was concentrated in vacuo. The crude residue was purified via silica gel chromatography (MeOH-DCM, 3-5%) to afford the title compound (130 mg, 81%). LCMS: m/z=755.3 (M−1).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe crude residue was purified via silica gel chromatography (MeOH-DCM, 3-5%)

Sources & evidence

ORD record
ord-a7cf692bc21142b997668082da38c555
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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