Trifluoroacetic acid → HCID 118379563, compound

HRID 708445Notes

Reaction equation

HRID 708445 reaction equation
C([O:5][C:6](=[O:55])[C:7]([O:10]/[N:11]=[C:12](/[C:42]1[N:43]=[C:44]([NH:47]C(OC(C)(C)C)=O)[S:45][CH:46]=1)\[C:13]([NH:15][C@@H:16]1[C:19](=[O:20])[N:18]([S:21]([OH:24])(=[O:23])=[O:22])[C@@H:17]1[CH2:25][N:26]1[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][NH:33]C(OC(C)(C)C)=O)[C:27]1=[O:41])=[O:14])([CH3:9])[CH3:8])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:33][CH2:32][CH2:31][N:28]1[CH2:29][CH2:30][N:26]([CH2:25][C@@H:17]2[C@H:16]([NH:15][C:13](=[O:14])/[C:12](=[N:11]\[O:10][C:7]([CH3:8])([CH3:9])[C:6]([OH:55])=[O:5])/[C:42]3[N:43]=[C:44]([NH2:47])[S:45][CH:46]=3)[C:19](=[O:20])[N:18]2[S:21]([OH:24])(=[O:22])=[O:23])[C:27]1=[O:41]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118379426HCID 118379426, compound

Product 1

HCID 118379563HCID 118379563, compoundYield 4.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Followed the general procedure for the acid mediated deprotection using (2R,3S)-3-((Z)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetamido)-2-((3-(2-((tert-butoxycarbonyl)amino)ethyl)-2-oxoimidazolidin-1-yl)methyl)-4-oxoazetidine-1-sulfonic acid (42 mg, 0.051 mmol), TFA (237 μl, 3.08 mmol) in DCM (500 μL). 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) to afford the title compound (1.2 mg, 4%). LC/MS: Rt=0.35 min, m/z=563.2 (M+1) Method 2m_acidic; 1H NMR (400 MHz, D2O): δ 1H NMR 6.99 (s, 1H), 5.32 (d, J=5.9 Hz, 1H), 4.56-4.50 (m, 1H), 3.70 (dd, J=15.1, 9.6 Hz, 1H), 3.59-3.49 (m, 1H), 3.46 3.30 (m, 4H), 3.29-3.20 (m, 2H), 3.08-3.02 (m, 2H), 1.40 (s, 3H), 1.38 (s, 3H).

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-9bff17fa683e4ea5bbc33b5d99be0b2a
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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