Trifluoroacetic acid → HCID 118379656, compound

HRID 708345Notes

Reaction equation

HRID 708345 reaction equation
C([O:5][C:6](=[O:45])[C:7]([O:10]/[N:11]=[C:12](/[C:32]1[N:33]=[C:34]([NH:37]C(OC(C)(C)C)=O)[S:35][CH:36]=1)\[C:13]([NH:15][C@H:16]1[C@@H:19]([CH2:20][N:21]2[CH2:25][CH2:24][O:23][C:22]2=[O:26])[N:18]([S:27]([OH:30])(=[O:29])=[O:28])[C:17]1=[O:31])=[O:14])([CH3:9])[CH3:8])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:37][C:34]1[S:35][CH:36]=[C:32](/[C:12](=[N:11]/[O:10][C:7]([CH3:9])([CH3:8])[C:6]([OH:45])=[O:5])/[C:13](=[O:14])[NH:15][C@H:16]2[C@@H:19]([CH2:20][N:21]3[CH2:25][CH2:24][O:23][C:22]3=[O:26])[N:18]([S:27]([OH:30])(=[O:29])=[O:28])[C:17]2=[O:31])[N:33]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118380155HCID 118380155, compound

Product 1

HCID 118379656HCID 118379656, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Followed the general procedure for the acid mediated deprotection using (3S,4R)-3-((Z)-2-(((1-(tert-butoxy)-2-methyl-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 (100 mg, 0.148 mmol), DCM (1.5 mL) and TFA (569 μl, 7.39 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 (10 mg, 12%) as a white solid. LCMS: Rt=0.32 min, m/z=521.0 (M+1) Method 2m_acidic; 1H NMR (400 MHz, DMSO-d6) δ 9.33 (d, J=8.8 Hz, 1H), 6.89 (s, 1H), 5.22 (dd, J=8.8, 5.7 Hz, 1H), 4.23-4.11 (m, 3H), 3.75-3.62 (m, 2H assumed; obscured by water), 3.60-3.51 (m, 1H assumed; obscured by water), 3.34 (dd, J=14.6, 5.5 Hz, 1H), 1.44 (s, 3H), 1.40 (s, 3H).

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-60a3e760d0e4404ab1ab3d9ac918982c
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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