HCID 118379508, compound → HCID 118380069, compound

HRID 708424Notes

Reaction equation

HRID 708424 reaction equation
[N:1]1[N:2]([CH2:6][C@@H:7]2[C@H:10]([NH:11][C:12](=[O:39])/[C:13](=[N:27]\[O:28][C:29]([CH3:38])([CH3:37])[C:30]([O:32]C(C)(C)C)=[O:31])/[C:14]3[N:15]=[C:16]([NH:19]C(OC(C)(C)C)=O)[S:17][CH:18]=3)[C:9](=[O:40])[N:8]2[S:41]([OH:44])(=[O:43])=[O:42])[N:3]=[CH:4][CH:5]=1>C(O)=O>[N:3]1[N:2]([CH2:6][C@@H:7]2[C@H:10]([NH:11][C:12](=[O:39])/[C:13](=[N:27]\[O:28][C:29]([CH3:38])([CH3:37])[C:30]([OH:32])=[O:31])/[C:14]3[N:15]=[C:16]([NH2:19])[S:17][CH:18]=3)[C:9](=[O:40])[N:8]2[S:41]([OH:44])(=[O:42])=[O:43])[N:1]=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 118379508HCID 118379508, compound

Product 1

HCID 118380069HCID 118380069, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

(2R,3S)-2-((2H-1,2,3-triazol-2-yl)methyl)-3-((Z)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetamido)-4-oxoazetidine-1-sulfonic acid (70 mg, 0.11 mmol) was stirred with formic acid (2.0 mL) at rt for 4 h then concentrated in vacuo. The crude residue was purified by reverse phase prep HPLC (XBridge, 30×100 mm, 5 μm, C18 column; ACN-water with 0.1% formic acid modifier, 1 mL/min), affording the title compound (8.1 mg, 15%) as a white solid. LCMS: m/z=500.9 (M−1); 1H NMR (400 MHz, D2O): δ 7.60 (s, 2H), 6.94 (s, 1H), 5.39 (d, J=5.2 Hz, 1H),), 4.83-4.78 (m, 2H), 4.78-4.68 (m, 1H assumed; obscured by solvent residual peak), 1.26 (s, 3H), 1.25 (s, 3H).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe crude residue was purified by reverse phase prep HPLC (XBridge, 30×100 mm, 5 μm, C18 column; ACN-water with 0.1% formic acid modifier, 1 mL/min)

Sources & evidence

ORD record
ord-ceaa9d07ed8e4ebcbb08ba89c9332954
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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