1-Hydroxybenzotriazole → HCID 131731727, compound

HRID 2400752Notes

Reaction equation

HRID 2400752 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C@@H:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]([NH:15][NH2:16])=[O:14])([CH3:4])([CH3:3])[CH3:2].[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.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6](=[O:17])[NH:7][C@@H:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]([NH:15][NH:16][C:35]([C@@H:30]1[CH2:29][CH2:28][C@@H:27]2[CH2:34][N:31]1[C:32](=[O:33])[N:26]2[O:25][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:36])=[O:14])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 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 EDCl (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-d474c4f06240461aa6d13d5897048215
Source dataset
uspto-grants-2014_08
Patent number
US08796257B2

Reaction notes

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