Trifluoroacetic acid → HCID 118379918, compound

HRID 708381Notes

Reaction equation

HRID 708381 reaction equation
[N:1]1([CH2:6][C@@H:7]2[C@H:10]([NH:11][C:12](=[O:37])/[C:13](=[N:27]\[O:28][CH2:29][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:38])[N:8]2[S:39]([OH:42])(=[O:41])=[O:40])[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:37])/[C:13](=[N:27]\[O:28][CH2:29][C:30]([OH:32])=[O:31])/[C:14]3[N:15]=[C:16]([NH2:19])[S:17][CH:18]=3)[C:9](=[O:38])[N:8]2[S:39]([OH:42])(=[O:40])=[O:41])[CH:5]=[N:4][CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118379537HCID 118379537, compound

Product 1

HCID 118379918HCID 118379918, compoundYield 31.1%

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-((2-(tert-butoxy)-2-oxoethoxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetamido)-4-oxoazetidine-1-sulfonic acid (97 mg, 0.154 mmol), DCM (1.54 mL) and TFA (711 μl, 9.23 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 (22.7 mg, 22%) as a white powder. LCMS: Rt=0.28 min, m/z=475.0 (M+1) Method 2m_acidic; 1H NMR (400 MHz, DMSO-d6) δ 9.50 (d, J=9.0 Hz, 1H), 8.56 (s, 1H), 8.07 (s, 1H), 6.80 (s, 1H), 5.25 (dd, J=9.0, 5.9 Hz, 1H), 4.69-4.49 (m, 4H), 4.36 (dt, J=7.4, 4.9 Hz, 1H).

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-b67c185e2ace4ac1a48fb241e5112c55
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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