Trifluoroacetic acid → HCID 118379385, compound

HRID 708509Notes

Reaction equation

HRID 708509 reaction equation
C([O:14][C:15]([C:17]1([O:20]/[N:21]=[C:22](/[C:56]2[N:57]=[C:58]([NH:61]C(OC(C)(C)C)=O)[S:59][CH:60]=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][NH:42][C:43](=[O:55])[O:44][CH2:45][CH2:46][NH:47]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>[NH2:47][CH2:46][CH2:45][O:44][C:43]([NH: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])[CH2:18][CH2:19]3)/[C:56]3[N:57]=[C:58]([NH2:61])[S:59][CH:60]=3)[C:29](=[O:30])[N:28]2[S:31]([OH:34])(=[O:32])=[O:33])[N:40]=1)=[O:55]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118379300HCID 118379300, compound

Product 1

HCID 118379385HCID 118379385, compoundYield 44.7%

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-(10,10-dimethyl-3,8-dioxo-4,9-dioxa-2,7-diazaundecyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidine-1-sulfonic acid (68 mg, 69 μmol), DCM (0.7 mL) and TFA (0.32 mL, 4.15 mmol). 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 (19 mg, 44%). LCMS: R=0.54 min, m/z=617.3 (M+1) Method 2m_acidic_polar; 1H NMR (400 MHz, D2O) δ 7.67 (s, 1H), 7.10 (s, 1H), 5.60-5.52 (m, 1H), 5.01-4.84 (m, 3H), 4.43-4.37 (s, 2H), 4.35-4.27 (m, 2H), 3.33-3.25 (m, 2H), 1.36-1.13 (m, 4H).

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-4941b1e48638452db0af44cafd6f74f1
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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