(-)-Benzyl (R)-glycidyl ether → HCID 118379647, compound

HRID 708446Notes

Reaction equation

HRID 708446 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.[CH2:37]([O:44][CH2:45][C@H:46]1[CH2:48][O:47]1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(Cl)Cl>[CH2:37]([O:44][CH2:45][C@H:46]([OH:47])[CH2:48][NH: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)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

4

Reactant 2

HCID 159746(-)-Benzyl (R)-glycidyl etherHCID 71491066HCID 71491066, compound

Product 1

HCID 118379647HCID 118379647, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared in analogous manner to example 63 step 1, using 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 (200 mg, 0.38 mmol), (R)-2-((benzyloxy)methyl)oxirane (623 mg, 3.8 mmol), DCM (2 mL). The crude residue was purified via silica gel chromatography (MeOH-DCM, 4-10%) to afford the title compound (126 mg, 48%). LCMS: m/z=691.3 (M+1).

Workup

  1. customPrepared in analogous manner to example 63 step 1
  2. customThe crude residue was purified via silica gel chromatography (MeOH-DCM, 4-10%)

Sources & evidence

ORD record
ord-f93b2a6ebf5646eeb1ad033d09d15846
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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