Trifluoroacetic acid → HCID 118379818, compound

HRID 708485Notes

Reaction equation

HRID 708485 reaction equation
C([O:14][C:15]([C:17]1([O:20]/[N:21]=[C:22](/[C:42]2[N:43]=[C:44]([NH:47]C(OC(C)(C)C)=O)[S:45][CH:46]=2)\[C:23]([NH:25][C@H:26]2[C@@H:29]([CH2:30][N:31]3[CH2:35][CH2:34][NH:33][C:32]3=[O:36])[N:28]([S:37]([OH:40])(=[O:39])=[O:38])[C:27]2=[O:41])=[O:24])[CH2:19][CH2:18]1)=[O:16])(C1C=CC=CC=1)C1C=CC=CC=1.C(OC(C1(O/N=C(/C2N=C(NC(OC(C)(C)C)=O)SC=2)\C(N[C@H]2[C@@H](CN3CCNC(=O)N3)N(S(O)(=O)=O)C2=O)=O)CC1)=O)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:47][C:44]1[S:45][CH:46]=[C:42](/[C:22](=[N:21]/[O:20][C:17]2([C:15]([OH:16])=[O:14])[CH2:18][CH2:19]2)/[C:23](=[O:24])[NH:25][C@H:26]2[C@@H:29]([CH2:30][N:31]3[CH2:35][CH2:34][NH:33][C:32]3=[O:36])[N:28]([S:37]([OH:40])(=[O:39])=[O:38])[C:27]2=[O:41])[N:43]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 118379328HCID 118379328, compoundHCID 118380127HCID 118380127, compound

Product 1

HCID 118379818HCID 118379818, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Followed the general procedure for the acid mediated deprotection using (3S,4R)-3-((Z)-2-((1-((benzhydryloxy)carbonyl)cyclopropoxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetamido)-2-oxo-4-((2-oxoimidazolidin-1-yl)methyl)azetidine-1-sulfonic acid, (3S,4R)-3-((Z)-2-((1-((benzhydryloxy)carbonyl)cyclopropoxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetamido)-2-oxo-4-((3-oxo-1,2,4-triazinan-1-yl)methyl)azetidine-1-sulfonic acid (48 mg, 61 μmol), DCM (0.61 mL), and TFA (0.28 mL, 3.7 mmol) for 4 h. 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) affording the title compound (3.6 mg, 10%). LCMS: Rt=0.45 min, m/z=518.1 (M+1), Method 2m_acidic; 1H NMR (500 MHz, D2O): δ 7.01 (s, 1H), 5.32 (d, J=5.5 Hz, 1H), 4.53-4.39 (m, 1H), 3.61 (dd, J=14.8, 6.9 Hz, 1H), 3.56-3.41 (m, 2H), 3.35-3.21 (m, 3H), 1.46-1.19 (m, 4H).

Workup

  1. customfor 4 h
  2. 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-2c2ea0b2941342469ad066e71a8b7382
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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