Trifluoroacetic acid → HCID 118379742, compound

HRID 708418Notes

Reaction equation

HRID 708418 reaction equation
C([O:5][C:6](=[O:52])[C:7]([O:10]/[N:11]=[C:12](/[C:39]1[N:40]=[C:41]([NH:44]C(OC(C)(C)C)=O)[S:42][CH:43]=1)\[C:13]([NH:15][C@@H:16]1[C:19](=[O:20])[N:18]([S:21]([O-:24])(=[O:23])=[O:22])[C@@H:17]1[CH2:25][N:26]1[CH:30]=[C:29]([C:31]2[CH:36]=[CH:35][N+:34]([CH3:37])=[CH:33][C:32]=2[CH3:38])[N:28]=[N:27]1)=[O:14])([CH3:9])[CH3:8])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:44][C:41]1[S:42][CH:43]=[C:39](/[C:12](=[N:11]/[O:10][C:7]([C:6]([OH:52])=[O:5])([CH3:9])[CH3:8])/[C:13]([NH:15][C@@H:16]2[C:19](=[O:20])[N:18]([S:21]([O-:24])(=[O:22])=[O:23])[C@@H:17]2[CH2:25][N:26]2[CH:30]=[C:29]([C:31]3[CH:36]=[CH:35][N+:34]([CH3:37])=[CH:33][C:32]=3[CH3:38])[N:28]=[N:27]2)=[O:14])[N:40]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118379690HCID 118379690, compound

Product 1

HCID 118379742HCID 118379742, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Followed the general procedure for the acid mediated deprotection using (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)-2-((4-(1,3-dimethylpyridin-1-ium-4-yl)-1H-1,2,3-triazol-1-yl)methyl)-4-oxoazetidine-1-sulfonate (24 mg, 0.032 mmol), DCM (1.2 mL) and TFA (0.3 mL, 3.9 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, 62%) as a white solid. LCMS: m/z=606.1 (M−1); 1H NMR (400 MHz, D2O): δ 8.65 (s, 1H), 8.57 (s, 1H), 8.49 (d, J=5.6 Hz, 1H), 8.27 (d, J=6.8 Hz, 1H), 6.74 (br s, 1H), 5.47 (d, J=5.2 Hz, 1H), 4.97-4.88 (m, 3H), 4.21 (s, 3H), 2.46 (s, 3H), 1.30 (s, 3H), 1.28 (s, 3H).

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-e5313db5ad2245aa94c1e4102edc3137
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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