Trifluoroacetic acid → HCID 118379868, compound

HRID 708487Notes

Reaction equation

HRID 708487 reaction equation
[NH2:1][CH2:2][C:3]1[C:7]([CH2:8][N:9](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=[N:6][N:5]([CH2:24][C@@H:25]2[C@H:28]([NH:29][C:30](=[O:66])/[C:31](=[N:45]\[O:46][C:47]3([C:50]([O:52]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:51])[CH2:49][CH2:48]3)/[C:32]3[N:33]=[C:34]([NH:37]C(OC(C)(C)C)=O)[S:35][CH:36]=3)[C:27](=[O:67])[N:26]2[S:68]([OH:71])(=[O:70])=[O:69])[N:4]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:37][C:34]1[S:35][CH:36]=[C:32](/[C:31](=[N:45]/[O:46][C:47]2([C:50]([OH:52])=[O:51])[CH2:49][CH2:48]2)/[C:30]([NH:29][C@@H:28]2[C:27](=[O:67])[N:26]([S:68]([OH:71])(=[O:69])=[O:70])[C@@H:25]2[CH2:24][N:5]2[N:6]=[C:7]([CH2:8][NH2:9])[C:3]([CH2:2][NH2:1])=[N:4]2)=[O:66])[N:33]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118380270HCID 118380270, compound

Product 1

HCID 118379868HCID 118379868, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Followed the general procedure for the acid mediated deprotection using (2R,3S)-2-((4-(aminomethyl)-5-((bis(tert-butoxycarbonyl)amino)methyl)-2H-1,2,3-triazol-2-yl)methyl)-3-((Z)-2-((1-((benzhydryloxy)carbonyl)cyclopropoxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetamido)-4-oxoazetidine-1-sulfonic acid (109 mg, 0.11 DCM (1.1 mL), and TFA (0.49 mL, 6.36 mmol) for 2 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 (12 mg, 19%). LCMS: Rt=0.46 min, m/z=559.2 (M+1), Method 2m_acidic; 1H NMR (400 MHz, D2O): δ 7.16 (s, 1H), 5.61 (d, J=5.6 Hz, 1H), 5.07-4.88 (m, 3H), 4.34 (s, 4H), 1.39-1.13 (m, 4H).

Workup

  1. customfor 2 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-61e6fb42f247477699d80fcd621ad881
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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