HCID 118380051, compound → HCID 118379921, compound

HRID 708425Notes

Reaction equation

HRID 708425 reaction equation
C([O:5][C:6](=[O:45])[C:7]([O:10]/[N:11]=[C:12](/[C:32]1[N:33]=[C:34]([NH:37]C(OC(C)(C)C)=O)[S:35][CH:36]=1)\[C:13]([NH:15][C@@H:16]1[C:19](=[O:20])[N:18]([S:21]([OH:24])(=[O:23])=[O:22])[C@@H:17]1[CH2:25][N:26]1[N:30]=[C:29]([CH3:31])[CH:28]=[N:27]1)=[O:14])([CH3:9])[CH3:8])(C)(C)C>C(O)=O>[NH2:37][C:34]1[S:35][CH:36]=[C:32](/[C:12](=[N:11]/[O:10][C:7]([CH3:9])([CH3:8])[C:6]([OH:45])=[O:5])/[C:13]([NH:15][C@@H:16]2[C:19](=[O:20])[N:18]([S:21]([OH:24])(=[O:22])=[O:23])[C@@H:17]2[CH2:25][N:26]2[N:30]=[C:29]([CH3:31])[CH:28]=[N:27]2)=[O:14])[N:33]=1

Participants

3

Reactant 1

HCID 118380051HCID 118380051, compound

Product 1

HCID 118379921HCID 118379921, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

(2R,3S)-3-((Z)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetamido)-2-((4-methyl-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidine-1-sulfonic acid (67 mg, 0.10 mmol) was stirred with formic acid (1.5 mL) at rt for 3.5 h then concentrated in vacuo. The crude residue was purified by reverse phase prep HPLC (XBridge, 30×100 mm, 5 μm, C18 column; ACN-water with 0.1% formic acid modifier, 1 mL/min), affording the title compound (13.7 mg, 27%) as a white solid. LCMS: m/z=514.9 (M−1); 1H NMR (400 MHz, D2O): δ 7.39 (s, 1H), 6.94 (s, 1H), 5.38 (d, J=5.6 Hz, 1H), 4.80-4.60 (m, 3H assumed; obscured by solvent residual peak), 2.10 (s, 3H), 1.26 (s, 3H), 1.25 (s, 3H).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe crude residue was purified by reverse phase prep HPLC (XBridge, 30×100 mm, 5 μm, C18 column; ACN-water with 0.1% formic acid modifier, 1 mL/min)

Sources & evidence

ORD record
ord-e4030828802343d4a3cc009569815c5e
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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