Trifluoroacetic acid → HCID 118379528, compound

HRID 708383Notes

Reaction equation

HRID 708383 reaction equation
[N:1]1([CH2:6][C@@H:7]2[C@H:10]([NH:11][C:12](=[O:48])/[C:13](=[N:27]\[O:28][C:29]3([C:32]([O:34]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:33])[CH2:31][CH2:30]3)/[C:14]3[N:15]=[C:16]([NH:19]C(OC(C)(C)C)=O)[S:17][CH:18]=3)[C:9](=[O:49])[N:8]2[S:50]([OH:53])(=[O:52])=[O:51])[CH:5]=[N:4][CH: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:48])/[C:13](=[N:27]\[O:28][C:29]3([C:32]([OH:34])=[O:33])[CH2:30][CH2:31]3)/[C:14]3[N:15]=[C:16]([NH2:19])[S:17][CH:18]=3)[C:9](=[O:49])[N:8]2[S:50]([OH:53])(=[O:51])=[O:52])[CH:5]=[N:4][CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118475510HCID 118475510, compound

Product 1

HCID 118379528HCID 118379528, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Followed the general procedure for the acid mediated deprotection using (2R,3S)-2-((1H-1,2,4-triazol-1-yl)methyl)-3-((Z)-2-((1-((benzhydryloxy)carbonyl)cyclopropoxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetamido)-4-oxoazetidine-1-sulfonic acid (164 mg, 0.214 mmol), DCM (2.14 mL) and TFA (989 μl, 12.8 mmol). The crude residue purified by reverse phase prep HPLC (XSelect CSH, 30×100 mm, 5 μm, C18 column; ACN-water with 0.1% formic acid modifier, 60 mL/min), affording the title compound (50 mg, 41%) as a white powder. LCMS: Rt=0.29 min, m/z=501.1 (M+1) Method 2m_acidic; 1H NMR (400 MHz, DMSO-d6) δ 9.31 (d, J=9.0 Hz, 1H), 8.59 (s, 1H), 8.09 (s, 1H), 6.83 (s, 1H), 5.26 (dd, J=9.0, 5.5 Hz, 1H), 4.67 (dd, J=14.5, 4.3 Hz, 1H), 4.49-4.39 (m, 1H), 4.33 (ddd, J=7.4, 5.5, 4.3 Hz, 1H), 1.34-1.27 (m, 4H).

Workup

  1. customThe crude residue purified by reverse phase prep HPLC (XSelect CSH, 30×100 mm, 5 μm, C18 column; ACN-water with 0.1% formic acid modifier, 60 mL/min)

Sources & evidence

ORD record
ord-bf9af5170d444534ade2910f5102b899
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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