Trifluoroacetic acid → HCID 178512064, compound

HRID 708407Notes

Reaction equation

HRID 708407 reaction equation
[N:1]1([CH2:6][C@@H:7]2[C@H:10]([NH:11][C:12](=[O:70])/[C:13](=[N:27]\[O:28][C@@H:29]([CH2:46][O:47][C:48]3[CH:53]=[CH:52][C:51]([C:54](=[NH:69])[NH:55][CH:56]4[CH2:61][CH2:60][N:59](C(OC(C)(C)C)=O)[CH2:58][CH2:57]4)=[CH:50][CH:49]=3)[C:30]([O:32]C(C3C=CC=CC=3)C3C=CC=CC=3)=[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:71])[N:8]2[S:72]([OH:75])(=[O:74])=[O:73])[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:70])/[C:13](=[N:27]\[O:28][C@@H:29]([CH2:46][O:47][C:48]3[CH:49]=[CH:50][C:51]([C:54](=[NH:69])[NH:55][CH:56]4[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]4)=[CH:52][CH:53]=3)[C:30]([OH:32])=[O:31])/[C:14]3[N:15]=[C:16]([NH2:19])[S:17][CH:18]=3)[C:9](=[O:71])[N:8]2[S:72]([OH:75])(=[O:74])=[O:73])[CH:5]=[N:4][CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178452994HCID 178452994, compound

Product 1

HCID 178512064HCID 178512064, compoundYield 20%

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-((((S)-1-(benzhydryloxy)-3-(4-(N-(1-(tert-butoxycarbonyl)piperidin-4-yl)carbamimidoyl)phenoxy)-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetamido)-4-oxoazetidine-1-sulfonic acid (0.085 mmol), DCM (850 μL) and TFA (327 μL, 4.25 mmol). The crude residue was purified by reverse phase prep HPLC (XSelect CSH, 19×100 mm, 5 μm, C18 column; ACN-water with 0.1% formic acid modifier, 24 mL/min), affording the title compound (12 mg, 17%) as a white powder. LCMS: Rt=0.41 min, m/z=706.2 (M+1) Method 2m_acidic_polar; 1H NMR (400 MHz, DMSO-d6) δ 9.55 (d, J=7.4 Hz, 1H) 9.40 (br s, 1H) 9.01 (br s, 1H) 8.53-8.71 (m, 1H) 8.41 (s, 1H) 7.92 (s, 1H) 7.67 (d, J=9.0 Hz, 2H) 7.21 (br s, 2H) 7.03 (d, J=7.8 Hz, 1H) 6.76 (s, 1H) 5.17-5.24 (m, 1H) 4.94 (d, J=3.9 Hz, 1H) 4.46-4.53 (m, 2H) 4.37-4.45 (m, 1H) 4.25-4.32 (m, 1H) 3.88 (br s, 1H) 3.39 (br s, 4H) 2.92 (t, J=11.5 Hz, 2H) 2.05-2.14 (m, 2H) 1.79 (d, J=11.0 Hz, 2H).

Workup

  1. customThe crude residue was purified by reverse phase prep HPLC (XSelect CSH, 19×100 mm, 5 μm, C18 column; ACN-water with 0.1% formic acid modifier, 24 mL/min)

Sources & evidence

ORD record
ord-2b44c4267a8e440e8218eb587185014f
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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