Trifluoroacetic acid → HCID 118379932, compound

HRID 708506Notes

Reaction equation

HRID 708506 reaction equation
C([O:14][C:15]([C:17]1([O:20]/[N:21]=[C:22](/[C:71]2[N:72]=[C:73]([NH:76]C(OC(C)(C)C)=O)[S:74][CH:75]=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]([CH2:60][CH2:61][CH2:62][NH:63]C(OC(C)(C)C)=O)[C:43]([NH:52]C(OC(C)(C)C)=O)=[N:44]C(OC(C)(C)C)=O)[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][CH2:62][CH2:61][CH2:60][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:71]3[N:72]=[C:73]([NH2:76])[S:74][CH:75]=3)[C:29](=[O:30])[N:28]2[S:31]([OH:34])(=[O:32])=[O:33])[N:40]=1)[C:43]([NH2:52])=[NH:44]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 140689320HCID 140689320, compound

Product 1

HCID 118379932HCID 118379932, compoundYield 8.2%

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-((2,3-bis(tert-butoxycarbonyl)-1-(3-((tert-butoxycarbonyl)amino)propyl)guanidino)methyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidine-1-sulfonic acid (118 mg, 99 μmol), DCM (2 mL) and TFA (2.0 mL, 26 mmol). The crude residue was purified via 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 (5.1 mg, 8%). LCMS: Rt=0.28 min, m/z=629.4 (M+1). Method 2m_acidic.

Workup

  1. customThe crude residue was purified via 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-df222da4f6854d16bbd6b04393a64796
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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