Trifluoroacetic acid → HCID 118379523, compound

HRID 708342Notes

Reaction equation

HRID 708342 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][CH2:23][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][CH2:23][C:22]3=[O:26])[N:18]([S:27]([OH:30])(=[O:28])=[O:29])[C:17]2=[O:31])[N:33]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118380156HCID 118380156, compound

Product 1

HCID 118379523HCID 118379523, compoundYield 16.1%

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-oxopyrrolidin-1-yl)methyl)azetidine-1-sulfonic acid (55 mg, 0.072 mmol), DCM (720 μL) and TFA (333 μL, 4.32 mmol). The crude residue was purified by reverse phase preperative 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 (6 mg, 16%) as a white solid. LCMS: Rt=0.35 min, m/z=519.0 (M+1) Method 2m_acidic; 1H NMR (400 MHz, D2O): δ 7.17 (s, 1H), 5.46 (d, J=5.8 Hz, 1H), 4.71-4.64 (m, 1H), 3.92 (dd, J=14.7, 8.7 Hz, 1H), 3.71-3.55 (m, 2H), 3.49 (dd, J=14.7, 4.1 Hz, 1H), 2.42 (td, J=8.0, 4.8 Hz, 2H), 2.08 (p, J=7.6 Hz, 2H), 1.55 (s, 3H), 1.54 (s, 3H).

Workup

  1. customThe crude residue was purified by reverse phase preperative 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-e48a1f92f8104b06b6a4288222fa986f
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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