Trifluoroacetic acid → HCID 118379828, compound

HRID 708387Notes

Reaction equation

HRID 708387 reaction equation
C([O:5][C:6](=[O:43])[CH2:7][O:8]/[N:9]=[C:10](/[C:30]1[N:31]=[C:32]([NH:35]C(OC(C)(C)C)=O)[S:33][CH:34]=1)\[C:11]([NH:13][C@H:14]1[C@@H:17]([CH2:18][N:19]2[CH2:23][CH2:22][O:21][C:20]2=[O:24])[N:16]([S:25]([OH:28])(=[O:27])=[O:26])[C:15]1=[O:29])=[O:12])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:35][C:32]1[S:33][CH:34]=[C:30](/[C:10](=[N:9]/[O:8][CH2:7][C:6]([OH:43])=[O:5])/[C:11](=[O:12])[NH:13][C@H:14]2[C@@H:17]([CH2:18][N:19]3[CH2:23][CH2:22][O:21][C:20]3=[O:24])[N:16]([S:25]([OH:28])(=[O:26])=[O:27])[C:15]2=[O:29])[N:31]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118380252HCID 118380252, compound

Product 1

HCID 118379828HCID 118379828, compoundYield 24.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Followed the general procedure for the acid mediated deprotection using (3S,4R)-3-((Z)-2-((2-(tert-butoxy)-2-oxoethoxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetamido)-2-oxo-4-((2-oxooxazolidin-3-yl)methyl)azetidine-1-sulfonic acid (135 mg, 0.208 mmol), DCM (1.04 mL) and TFA (801 μl, 10.4 mmol). The crude residue 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 (25 mg, 23%) as a white powder. LCMS: Rt=0.25 min, m/z=493.0 (M+1) Method 2m_acidic; 1H NMR (500 MHz, DMSO-d6) δ 9.41 (d, J=9.1 Hz, 1H) 6.86 (s, 1H) 5.24 (dd, J=9.0, 5.8 Hz, 1H) 4.62 (s, 2H) 4.20-4.11 (m, 3H) 3.72-3.63 (m, 2H) 3.40-3.31 (m, 2H assumed; obscured by water).

Workup

  1. customThe crude residue 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-c741b1c62e9b441883fce2355ae4a3ad
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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