Piperidine → benzhydryl 1-[(Z)-[2-[[(2R,3S)-2-[(2-aminoethylamino)methyl]-4-oxoazetidin-3-yl]amino]-1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-oxoethylidene]amino]oxycyclopropane-1-carboxylate

HRID 708483Notes

Reaction equation

HRID 708483 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:64])/[C:29](=[N:43]\[O:44][C:45]4([C:48]([O:50][CH:51]([C:58]5[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=5)[C:52]5[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=5)=[O:49])[CH2:47][CH2:46]4)/[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:65])[NH:24]3)=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>C(Cl)Cl>[NH2:18][CH2:19][CH2:20][NH:21][CH2:22][C@@H:23]1[C@H:26]([NH:27][C:28](=[O:64])/[C:29](=[N:43]\[O:44][C:45]2([C:48]([O:50][CH:51]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)=[O:49])[CH2:46][CH2:47]2)/[C:30]2[N:31]=[C:32]([NH:35][C:36]([O:38][C:39]([CH3:40])([CH3:42])[CH3:41])=[O:37])[S:33][CH:34]=2)[C:25](=[O:65])[NH:24]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 118379524benzhydryl 1-[(Z)-[2-[[(2R,3S)-2-[[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethylamino]methyl]-4-oxoazetidin-3-yl]amino]-1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-oxoethylidene]amino]oxycyclopropane-1-carboxylate

Product 1

HCID 118379472benzhydryl 1-[(Z)-[2-[[(2R,3S)-2-[(2-aminoethylamino)methyl]-4-oxoazetidin-3-yl]amino]-1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-oxoethylidene]amino]oxycyclopropane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzhydryl 1-(((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)cyclopropanecarboxylate (150 mg, 0.167 mmol) in DCM (1.7 mL) was added piperidine (16.50 μl, 0.167 mmol). After 2 h, the reaction mixture was concentrated in vacuo and lyophilized in CH3CN/water mixture to afford the title compound (assumed quantitative). LCMS: Rt=0.93 min, m/z=678.5 (M+1), Method 2m_acidic.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-3d6508e0f5db41958601bafdb2b957c2
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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