tert-Butyl (3-aminopropyl)carbamate → benzhydryl 1-[(Z)-[2-[[(2R,3S)-2-[[4-[[3-[(2-methylpropan-2-yl)oxycarbonylamino]propylamino]methyl]triazol-2-yl]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 708468Notes

Reaction equation

HRID 708468 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:31]/[O:32][C:33]2([C:36]([O:38][CH:39]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[O:37])[CH2:35][CH2:34]2)/[C:15]([NH:17][C@@H:18]2[C:21](=[O:22])[NH:20][C@@H:19]2[CH2:23][N:24]2[N:28]=[C:27]([CH:29]=O)[CH:26]=[N:25]2)=[O:16])[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:52]([O:56][C:57](=[O:63])[NH:58][CH2:59][CH2:60][CH2:61][NH2:62])([CH3:55])([CH3:54])[CH3:53].[Na]>ClCCCl.C(Cl)Cl>[C:52]([O:56][C:57]([NH:58][CH2:59][CH2:60][CH2:61][NH:62][CH2:29][C:27]1[CH:26]=[N:25][N:24]([CH2:23][C@@H:19]2[C@H:18]([NH:17][C:15](=[O:16])/[C:14](=[N:31]\[O:32][C:33]3([C:36]([O:38][CH:39]([C:46]4[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=4)[C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[O:37])[CH2:34][CH2:35]3)/[C:12]3[N:13]=[C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[S:10][CH:11]=3)[C:21](=[O:22])[NH:20]2)[N:28]=1)=[O:63])([CH3:55])([CH3:53])[CH3:54]

Participants

6

Reactant 3

HCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 5360545SodiumHCID 118379394benzhydryl 1-[(Z)-[2-[[(2R,3S)-2-[(4-formyltriazol-2-yl)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 118380067benzhydryl 1-[(Z)-[2-[[(2R,3S)-2-[[4-[[3-[(2-methylpropan-2-yl)oxycarbonylamino]propylamino]methyl]triazol-2-yl]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 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of benzhydryl 1-(((Z)-(1-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-(((2R,3S)-2-((4-formyl-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)cyclopropanecarboxylate (370 mg, 0.52 mmol) in DCE (4 mL) at 0° C. was added tert-butyl(3-aminopropyl)carbamate (180 mg, 1.04 mmol) and sodium triacetoxyhydroborate (165 mg, 0.78 mmol) sequentially. After stirring at rt for 16 h, the reaction mixture was diluted with DCM, washed with saturated NaHCO3 (aq), brine, dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (assumed quantitative). The crude residue was used as such in the following step. LCMS: Rt=0.99 min, m/z=873.2 (M+1). Method 2m_acidic.

Workup

  1. washwashed with saturated NaHCO3 (aq), brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5b3847a9b1ea43e6a1acaf5875e85759
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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