HCID 118379930, compound → HCID 118379618, compound

HRID 708416Notes

Reaction equation

HRID 708416 reaction equation
FC(F)(F)[S:3]([O-:6])(=[O:5])=[O:4].[C:9]([O:13][C:14](=[O:55])[C:15]([O:18]/[N:19]=[C:20](/[C:42]1[N:43]=[C:44]([NH:47][C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[S:45][CH:46]=1)\[C:21]([NH:23][C@@H:24]1[C:27](=[O:28])[NH:26][C@@H:25]1[CH2:29][N:30]1[CH:34]=[C:33]([C:35]2[CH:40]=[CH:39][N+:38]([CH3:41])=[CH:37][CH:36]=2)[N:32]=[N:31]1)=[O:22])([CH3:17])[CH3:16])([CH3:12])([CH3:11])[CH3:10]>CN(C=O)C>[C:9]([O:13][C:14](=[O:55])[C:15]([O:18]/[N:19]=[C:20](/[C:42]1[N:43]=[C:44]([NH:47][C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[S:45][CH:46]=1)\[C:21]([NH:23][C@@H:24]1[C:27](=[O:28])[N:26]([S:3]([O-:6])(=[O:5])=[O:4])[C@@H:25]1[CH2:29][N:30]1[CH:34]=[C:33]([C:35]2[CH:36]=[CH:37][N+:38]([CH3:41])=[CH:39][CH:40]=2)[N:32]=[N:31]1)=[O:22])([CH3:16])[CH3:17])([CH3:10])([CH3:11])[CH3:12]

Participants

3

Reactant 1

HCID 118379930HCID 118379930, compound

Product 1

HCID 118379618HCID 118379618, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-(1-(((2R,3S)-3-((Z)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetamido)-4-oxoazetidin-2-yl)methyl)-1H-1,2,3-triazol-4-yl)-1-methylpyridin-1-ium trifluoromethanesulfonate (70 mg, 0.10 mmol) in DMF (1 mL) was treated with SO3.DMF (80 mg, 0.52 mmol). The reaction mixture was stirred at rt for 16 h then concentrated in vacuo and purified by HP21 resin (ACN-water, 10-100%), affording the title compound (24 mg, 31%) as a beige solid. LCMS: m/z=748.1 (M−1).

Workup

  1. concentrationthen concentrated in vacuo
  2. custompurified by HP21 resin (ACN-water, 10-100%)

Sources & evidence

ORD record
ord-f6c3d65a32054079a6e7aba246ebf46a
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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