Piperidine → HCID 118380329, compound

HRID 708346Notes

Reaction equation

HRID 708346 reaction equation
C1C2C(COC([NH:18][CH2:19][CH2:20][NH:21][CH2:22][C@@H:23]3[C@H:26]([NH:27][C:28](=[O:55])/[C:29](=[N:43]\[O:44][C:45]([CH3:54])([CH3:53])[C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])/[C:30]4[N:31]=[C:32]([NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[S:33][CH:34]=4)[C:25](=[O:56])[NH:24]3)=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>CN(C=O)C.C1(C)C=CC=CC=1>[NH2:18][CH2:19][CH2:20][NH:21][CH2:22][C@@H:23]1[C@H:26]([NH:27][C:28](=[O:55])/[C:29](=[N:43]\[O:44][C:45]([CH3:54])([CH3:53])[C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])/[C:30]2[N:31]=[C:32]([NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[S:33][CH:34]=2)[C:25](=[O:56])[NH:24]1

Participants

5

Reactant 2

HCID 8082PiperidineHCID 118379767HCID 118379767, compound

Product 1

HCID 118380329HCID 118380329, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl 2-(((Z)-(2-(((2R,3S)-2-(((2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)ethyl)amino)methyl)-4-oxoazetidin-3-yl)amino)-1-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-oxoethylidene)amino)oxy)-2-methylpropanoate (435 mg, 0.549 mmol) in DMF (2.75 mL) was treated with piperidine (1.1 mL, 11 mmol). After stirring at rt for 1 h it was diluted with toluene and concentrated (3×). The crude residue was purified by reverse phase prep HPLC (XSelect CSH, 19×100 mm, 5 μm, C18 column; ACN-water with 0.1% formic acid modifier, 24 mL/min), affording the title compound (238 mg, 64%) as a white powder. LCMS: Rt=0.68 min, m/z=570.3 (M+1) Method 2m_acidic; 1H NMR (400 MHz, DMSO-d6) δ 9.12 (d, J=8.9 Hz, 1H), 8.38 (s, 1H), 8.31 (s, 1H), 7.21 (s, 1H), 5.17 (dd, J=8.3, 4.9 Hz, 1H), 3.76 (dt, J=8.7, 4.7 Hz, 1H), 2.81-2.51 (m, 6H), 1.44 (s, 9H), 1.41 (s, 3H), 1.39 (s, 3H), 1.38 (s, 9H).

Workup

  1. concentrationconcentrated (3×)
  2. customThe crude residue was purified by reverse phase prep HPLC (XSelect CSH, 19×100 mm, 5 μm, C18 column; ACN-water with 0.1% formic acid modifier, 24 mL/min)

Sources & evidence

ORD record
ord-96e139e554844ddf80162a95e47921fa
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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