Trifluoroacetic acid → HCID 118390880, compound

HRID 708420Notes

Reaction equation

HRID 708420 reaction equation
[N:1]1([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])[CH:5]=[CH:4][N:3]=[N:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:1]1([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])[CH:5]=[CH:4][N:3]=[N:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118475565HCID 118475565, compound

Product 1

HCID 118390880HCID 118390880, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Followed the general procedure for the acid mediated deprotection using (2R,3S)-2-((1H-1,2,3-triazol-1-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 (80 mg, 0.121 mmol), DCM (4 mL) and TFA (1 mL, 13 mmol). The crude residue was purified by reverse phase prep HPLC (T3, 30×150 mm, 5 μm, C18 column; ACN-water with 0.1% formic acid modifier, 1 mL/min), affording the title compound (12 mg, 20%) as a white solid. LCMS: m/z=500.9 (M−1); 1H NMR (400 MHz, D2O): δ 7.95 (s, 1H), 7.67 (s, 1H), 7.04 (s, 1H), 5.38 (d, J=5.6 Hz, 1H), 4.88-4.80 (m, 1H), 4.78-4.70 (m, 2H assumed; obscured by solvent residual peak), 1.34 (s, 6H).

Workup

  1. customThe crude residue was purified by reverse phase prep HPLC (T3, 30×150 mm, 5 μm, C18 column; ACN-water with 0.1% formic acid modifier, 1 mL/min)

Sources & evidence

ORD record
ord-f3e1eacbb4334a3ab6751dd874743b35
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

Loading…