HCID 71491066, compound → HCID 140689347, compound

HRID 708436Notes

Reaction equation

HRID 708436 reaction equation
[NH2:1][CH2:2][C@@H:3]1[C@H:6]([NH:7][C:8](=[O:35])/[C:9](=[N:23]\[O:24][C:25]([CH3:34])([CH3:33])[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])/[C:10]2[N:11]=[C:12]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[S:13][CH:14]=2)[C:5](=[O:36])[NH:4]1.[CH3:37][Si:38]([CH3:49])([CH3:48])[CH2:39][CH2:40][O:41][CH2:42][O:43][CH2:44][C@@H:45]1[CH2:47][O:46]1>C(Cl)Cl>[C:19]([O:18][C:16]([NH:15][C:12]1[S:13][CH:14]=[C:10](/[C:9](=[N:23]/[O:24][C:25]([CH3:34])([CH3:33])[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])/[C:8]([NH:7][C@@H:6]2[C:5](=[O:36])[NH:4][C@@H:3]2[CH2:2][NH:1][CH2:47][C@H:45]([OH:46])[CH2:44][O:43][CH2:42][O:41][CH2:40][CH2:39][Si:38]([CH3:49])([CH3:48])[CH3:37])=[O:35])[N:11]=1)=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 71491066HCID 71491066, compoundHCID 125500245HCID 125500245, compound2×

Product 1

HCID 140689347HCID 140689347, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(((Z)-(2-(((2R,3S)-2-(aminomethyl)-4-oxoazetidin-3-yl)amino)-1-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-oxoethylidene)amino)oxy)-2-methylpropanoate (500 mg, 0.95 mmol) in DCM (5 mL) was added (S)-trimethyl(2-((oxiran-2-ylmethoxy)methoxy)ethyl)silane (485 mg, 2.38 mmol). After stirring at rt for 12 h, another 2.5 equiv of (S)-trimethyl(2-((oxiran-2-ylmethoxy)methoxy)ethyl)silane was added. After stirring at rt for additional 12 h, the reaction mixture was concentrated in vacuo. The crude residue was purified via silica gel chromatography (MeOH-DCM, 2-10%) to afford the title compound (155 mg, 22%). LCMS: m/z=731.4 (M+1).

Workup

  1. stirringAfter stirring at rt for additional 12 h
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customThe crude residue was purified via silica gel chromatography (MeOH-DCM, 2-10%)

Sources & evidence

ORD record
ord-9b245d4928534042ad7d525777972ccb
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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