1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 131731727, compound

HRID 1053477Notes

Reaction equation

HRID 1053477 reaction equation
[NH:1]([C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:4])[NH2:2].[CH2:18]([O:25][N:26]1[C:32](=[O:33])[N:31]2[CH2:34][C@H:27]1[CH2:28][CH2:29][C@H:30]2[C:35](O)=[O:36])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:18]([O:25][N:26]1[C:32](=[O:33])[N:31]2[CH2:34][C@H:27]1[CH2:28][CH2:29][C@H:30]2[C:35]([NH:2][NH:1][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:4])=[O:36])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 57389355(2S,5R)-6-(Benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acidHCID 90228933HCID 90228933, compound

Product 1

HCID 131731727HCID 131731727, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl [(1R,2R)-2-(hydrazinylcarbonyl)cyclopentyl]carbamate 285 (0.15 g, 0.54 mmol) in 20 mL of DCM were added compound 1 (0.2 g, 0.82 mmol), HOBt (0.11 g, 0.82 mmol), DMAP (0.2 g, 1.64 mmol) and EDCI (0.16 g, 0.82 mmol). The mixture was stirred at room temperature for 18 h and purified by column chromatography to afford compound 286 as a solid (0.22 g, 82%).

Workup

  1. custompurified by column chromatography

Sources & evidence

ORD record
ord-36e0dd0899d34db9b9a6105f98c3c630
Source dataset
uspto-grants-2016_07
Patent number
US09393239B2

Reaction notes

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