Trifluoroacetic acid → HCID 118380196, compound

HRID 708511Notes

Reaction equation

HRID 708511 reaction equation
C([O:14][C:15]([C:17]1([O:20]/[N:21]=[C:22](/[C:58]2[N:59]=[C:60]([NH:63]C(OC(C)(C)C)=O)[S:61][CH:62]=2)\[C:23]([NH:25][C@@H:26]2[C:29](=[O:30])[N:28]([S:31]([O-:34])(=[O:33])=[O:32])[C@@H:27]2[CH2:35][N:36]2[N:40]=[C:39]([CH2:41][N:42](C(OC(C)(C)C)=O)[CH2:43][C:44]3[CH:45]=[N+:46]([CH3:50])[CH:47]=[CH:48][CH:49]=3)[CH:38]=[N:37]2)=[O:24])[CH2:19][CH2:18]1)=[O:16])(C1C=CC=CC=1)C1C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:63][C:60]1[S:61][CH:62]=[C:58](/[C:22](=[N:21]/[O:20][C:17]2([C:15]([OH:16])=[O:14])[CH2:18][CH2:19]2)/[C:23]([NH:25][C@@H:26]2[C:29](=[O:30])[N:28]([S:31]([O-:34])(=[O:32])=[O:33])[C@@H:27]2[CH2:35][N:36]2[N:40]=[C:39]([CH2:41][NH:42][CH2:43][C:44]3[CH:45]=[N+:46]([CH3:50])[CH:47]=[CH:48][CH:49]=3)[CH:38]=[N:37]2)=[O:24])[N:59]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118380212HCID 118380212, compound

Product 1

HCID 118380196HCID 118380196, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Followed the general procedure for the acid mediated deprotection using (2R,3S)-3-((Z)-2-((1-((benzhydryloxy)carbonyl)cyclopropoxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetamido)-2-((4-(((tert-butoxycarbonyl)((1-methylpyridin-1-ium-3-yl)methyl)amino)methyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidine-1-sulfonate (53 mg, 0.053 mmol), TFA (81 μl, 1.1 mmol) and DCM (72 mL). The crude residue purified by reverse phase prep HPLC (Xselect CSH, 30×100 mm, C18 column; ACN-water with 0.1% formic acid modifier, 60 mL/min), affording the title compound (13 mg, 35%) as a white powder. LCMS: Rt=0.30 min, m/z=635.3 (M+1) Method 2m_acidic; 1H NMR (400 MHz, D2O) δ 9.00 (s, 1H), 8.78-8.67 (m, 2H), 7.97 (t, J=7.1 Hz, 1H), 7.86 (s, 1H), 6.93 (s, 1H), 5.75 (d, J=5.3 Hz, 1H), 5.11 (dd, J=14.4, 3.7 Hz, 1H), 5.06-4.99 (m, 1H), 4.70-4.46 (m, 4H), 4.38 (s, 3H), 3.77-3.62 (m, 1H), 1.35-1.26 (m, 1H), 1.20-1.10 (m, 2H), 0.93-0.82 (m, 1H).

Workup

  1. customThe crude residue purified by reverse phase prep HPLC (Xselect CSH, 30×100 mm, C18 column; ACN-water with 0.1% formic acid modifier, 60 mL/min)

Sources & evidence

ORD record
ord-83ab367a3e9a4e2ca8aecaed7c6d2c7d
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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