Trifluoroacetic acid → HCID 178482993, compound

HRID 708534Notes

Reaction equation

HRID 708534 reaction equation
C([O:14][C:15]([C:17]1([O:20]/[N:21]=[C:22](/[C:72]2[N:73]=[C:74]([NH:77]C(OC(C)(C)C)=O)[S:75][CH:76]=2)\[C:23]([NH:25][C@@H:26]2[C:29](=[O:30])[N:28]([S:31]([OH:34])(=[O:33])=[O:32])[C@@H:27]2[CH2:35][N:36]2[N:40]=[C:39]([CH2:41][N:42]([CH3:71])[C:43](=[N:63]C(OC(C)(C)C)=O)[N:44](C(OC(C)(C)C)=O)[CH2:45][CH2:46][CH2:47][NH:48]C(=O)OC(C)(C)C)[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>[NH2:48][CH2:47][CH2:46][CH2:45][NH:44][C:43](=[NH:63])[N:42]([CH2:41][C:39]1[CH:38]=[N:37][N:36]([CH2:35][C@@H:27]2[C@H:26]([NH:25][C:23](=[O:24])/[C:22](=[N:21]\[O:20][C:17]3([C:15]([OH:16])=[O:14])[CH2:19][CH2:18]3)/[C:72]3[N:73]=[C:74]([NH2:77])[S:75][CH:76]=3)[C:29](=[O:30])[N:28]2[S:31]([OH:34])(=[O:32])=[O:33])[N:40]=1)[CH3:71]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118380044HCID 118380044, compound

Product 1

HCID 178482993HCID 178482993, compoundYield 7.8%

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-(4-(tert-butoxycarbonyl)-3-((tert-butoxycarbonyl)imino)-2,11,11-trimethyl-9-oxo-10-oxa-2,4,8-triazadodecyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidine-1-sulfonic acid (27 mg, 0.022 mmol), TFA (103 μl, 1.34 mmol) and DCM (223 μl). The crude material was purified by reverse phase preparative HPLC (XSELECT C18, 5μ, 30×100 mm, ACN/H2O w/0.1% formic acid buffer), affording the title compound (1.1 mg, 7%) as a white solid. LCMS: Rt=0.32 min, m/z=643.3 (M+1) Method 2m_acidic. 1H NMR (500 MHz, D2O) δ ppm 7.65 (s, 1H) 7.00 (s, 1H) 5.48 (d, J=5.7 Hz, 1H) 4.89-4.83 (m, 1H) 4.60-4.45 (m, 2H) 3.25 (td, J=6.9, 3.6 Hz, 2H) 2.95 (t, J=7.7 Hz, 2H) 2.91 (s, 3H) 1.98-1.74 (m, 2H) 1.23-1.10 (m, 2H) 1.05-1.00 (m, 2H).

Workup

  1. customThe crude material was purified by reverse phase preparative HPLC (XSELECT C18, 5μ, 30×100 mm, ACN/H2O w/0.1% formic acid buffer)

Sources & evidence

ORD record
ord-5aacecaa8c6846db9f0be0fd7e8a1783
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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