Trifluoroacetic acid → HCID 178512063, compound

HRID 708439Notes

Reaction equation

HRID 708439 reaction equation
C([O:14][C:15](=[O:76])[C@@H:16]([O:41]/[N:42]=[C:43](/[C:63]1[N:64]=[C:65]([NH:68]C(OC(C)(C)C)=O)[S:66][CH:67]=1)\[C:44]([NH:46][C@H:47]1[C@@H:50]([CH2:51][N:52]2[CH2:56][CH2:55][O:54][C:53]2=[O:57])[N:49]([S:58]([OH:61])(=[O:60])=[O:59])[C:48]1=[O:62])=[O:45])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=[NH:40])[NH:26][CH:27]2[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]2)=[CH:21][CH:20]=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:68][C:65]1[S:66][CH:67]=[C:63](/[C:43](=[N:42]/[O:41][C@@H:16]([CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25](=[NH:40])[NH:26][CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)=[CH:21][CH:20]=2)[C:15]([OH:76])=[O:14])/[C:44](=[O:45])[NH:46][C@H:47]2[C@@H:50]([CH2:51][N:52]3[CH2:56][CH2:55][O:54][C:53]3=[O:57])[N:49]([S:58]([OH:61])(=[O:59])=[O:60])[C:48]2=[O:62])[N:64]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178452993HCID 178452993, compound

Product 1

HCID 178512063HCID 178512063, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Followed the general procedure for the acid mediated deprotection using (3S,4R)-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)-2-oxo-4-((2-oxooxazolidin-3-yl)methyl)azetidine-1-sulfonic acid (117 mg, 0.107 mmol), DCM (5.3 mL) and TFA (0.413 mL, 5.37 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 (23 mg, 28%) as a white powder. LC/MS: Rt=0.42 min, m/z=724.5 (M+1) Method 2m_acidic_polar; 1H NMR (500 MHz, DMSO-d6) δ 9.53 (d, J=7.57 Hz, 1H), 9.43-9.36 (m, 2H), 9.01 (br s, 1H), 8.53-8.36 (m, 2H), 7.72 (d, J=8.5 Hz, 3H), 7.26 (br s, 2H), 7.15 (d, J=8.8 Hz, 2H), 6.82 (s, 1H), 5.19 (dd, J=8.7, 5.8 Hz, 1H), 5.02 (t, J=3.8 Hz, 1H), 4.51-4.42 (m, 2H), 4.12-3.96 (m, 3H), 3.90-3.81 (m, 1H), 3.73 (d, J=7.3 Hz, 1H), 3.69-3.62 (m, 1H), 3.58-3.53 (m, 1H), 3.20-3.16 (m, 1H), 2.98-2.85 (m, 1H) 2.13-2.04 (m, 1H), 1.85-1.72 (m, 1H).

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-24e01f2426304325be2d727e6bb45a7c
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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