Trifluoroacetic acid → HCID 118379760, compound

HRID 708421Notes

Reaction equation

HRID 708421 reaction equation
C([O:5][C:6](=[O:51])[C:7]([O:10]/[N:11]=[C:12](/[C:38]1[N:39]=[C:40]([NH:43]C(OC(C)(C)C)=O)[S:41][CH:42]=1)\[C:13]([NH:15][C@@H:16]1[C:19](=[O:20])[N:18]([S:21]([OH:24])(=[O:23])=[O:22])[C@@H:17]1[CH2:25][N:26]1[CH:30]=[C:29]([C:31]([O:33]C(C)(C)C)=[O:32])[N:28]=[N:27]1)=[O:14])([CH3:9])[CH3:8])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:43][C:40]1[S:41][CH:42]=[C:38](/[C:12](=[N:11]/[O:10][C:7]([C:6]([OH:51])=[O:5])([CH3:9])[CH3:8])/[C:13]([NH:15][C@@H:16]2[C:19](=[O:20])[N:18]([S:21]([OH:24])(=[O:22])=[O:23])[C@@H:17]2[CH2:25][N:26]2[CH:30]=[C:29]([C:31]([OH:33])=[O:32])[N:28]=[N:27]2)=[O:14])[N:39]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118379517HCID 118379517, compound

Product 1

HCID 118379760HCID 118379760, compoundYield 27%

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-(tert-butoxycarbonyl)-1H-1,2,3-triazol-1-yl)methyl)-4-oxoazetidine-1-sulfonic acid (180 mg, 0.237 mmol), DCM (8 mL) and TFA (2 mL, 26 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 (35 mg, 27%) as a white solid. LCMS: m/z=544.9 (M−1); 1H NMR (400 MHz, D2O): δ 8.43 (s, 1H), 6.99 (s, 1H), 5.38 (d, J=5.2 Hz, 1H), 4.92-4.71 (m, 3H; partially obscured by solvent residual peak), 1.33 (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-058e2e24d22843b6beba2ce66a301492
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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