Trifluoroacetic acid → HCID 178460217, compound

HRID 708413Notes

Reaction equation

HRID 708413 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:45]/[O:46][C:47]([CH3:52])([CH3:51])[C:48]([OH:50])=[O:49])/[C:8]([NH:10][C@@H:11]2[C:14](=[O:15])[N:13]([S:16]([OH:19])(=[O:18])=[O:17])[C@@H:12]2[CH2:20][N:21]2[CH:25]=[C:24]([CH2:26][NH:27][C:28]([NH:37]C(OC(C)(C)C)=O)=[N:29]C(OC(C)(C)C)=O)[N:23]=[N:22]2)=[O:9])[N:6]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:45]/[O:46][C:47]([CH3:52])([CH3:51])[C:48]([OH:50])=[O:49])/[C:8]([NH:10][C@@H:11]2[C:14](=[O:15])[N:13]([S:16]([OH:19])(=[O:17])=[O:18])[C@@H:12]2[CH2:20][N:21]2[CH:25]=[C:24]([CH2:26][NH:27][C:28]([NH2:37])=[NH:29])[N:23]=[N:22]2)=[O:9])[N:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178454250HCID 178454250, compound

Product 1

HCID 178460217HCID 178460217, compoundYield 3.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(((Z)-(1-(2-aminothiazol-4-yl)-2-(((2R,3S)-2-((4-((2,3-bis(tert-butoxycarbonyl)guanidino)methyl)-1H-1,2,3-triazol-1-yl)methyl)-4-oxo-1-sulfoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid (0.15 mmol, assumed quantitative conversion) In DCM (1.5 mL) at 0° C. was added TFA (689 μL, 9 mmol). The cold bath was removed after 10 min. After 4 h at rt it was diluted with DCM (1.5 mL) and concentrated in vacuo. The crude residue was purified by reverse phase prep HPLC (X-Bridge, 30×100 mm, 5 μm, C18 column; acetonitrile-water with 0.1% formic acid modifier, 1 mL/min) to afford the title compound (2.7 mg, 3%). LCMS: m/z=572.0 (M−1); 1H NMR (400 MHz, D2O): δ 1H NMR (400 MHz, D2O): δ 7.91 (s, 1H), 6.80 (s, 1H), 5.31 (d, J=5.2 Hz, 1H), 4.54 (s, 1H), 4.35 (s, 2H), 3.50-3.35 (m, 2H), 1.19 (s, 3H), 1.18 (s, 3H).

Workup

  1. customThe cold bath was removed after 10 min
  2. additionAfter 4 h at rt it was diluted with DCM (1.5 mL)
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was purified by reverse phase prep HPLC (X-Bridge, 30×100 mm, 5 μm, C18 column; acetonitrile-water with 0.1% formic acid modifier, 1 mL/min)

Sources & evidence

ORD record
ord-84a167e14b0c4fb385d66974a749933f
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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