Trifluoroacetic acid → HCID 118380146, compound

HRID 708405Notes

Reaction equation

HRID 708405 reaction equation
[N:1]1([CH2:6][C@@H:7]2[C@H:10]([NH:11][C:12](=[O:38])/[C:13](=[N:27]\[O:28][C@H:29]([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:39])[N:8]2[S:40]([OH:43])(=[O:42])=[O:41])[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:38])/[C:13](=[N:27]\[O:28][C@H:29]([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:39])[N:8]2[S:40]([OH:43])(=[O:41])=[O:42])[CH:5]=[N:4][CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118475513HCID 118475513, compound

Product 1

HCID 118380146HCID 118380146, compoundYield 33.2%

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-((((R)-1-(tert-butoxy)-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetamido)-4-oxoazetidine-1-sulfonic acid (141 mg, 0.219 mmol), DCM (2.19 mL) and TFA (1.0 mL, 13 mmol). The crude residue was 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 (35.5 mg, 29%) as a white powder. LCMS: Rt=0.42 min, m/z=489.0 (M+1) Method 2m_acidic_polar; 1H NMR (400 MHz, D2O) δ 8.58 (s, 1H), 8.06 (s, 1H), 7.06 (s, 1H), 5.41 (d, J=5.6 Hz, 1H), 4.81-4.52 (m, 4H assumed; partly obscured by solvent peak), 1.29 (d, J=7.0 Hz, 3H).

Workup

  1. customThe crude residue was 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-1dc29eacebea437a94c5b6ae500cca31
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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