1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 86659598, compound

HRID 451324Notes

Reaction equation

HRID 451324 reaction equation
Cl.CN(C)CCCN=C=NCC.[C:13]1([CH2:19][O:20][N:21]2[C:27](=[O:28])[N:26]3[CH2:29][C@H:22]2[CH2:23][CH2:24][C@H:25]3[C:30]([OH:32])=[O:31])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O[CH2:34][CH:35]1[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37][CH2:36]1>CN(C)C1C=CN=CC=1.ClCCl>[CH2:19]([O:20][N:21]1[C:27](=[O:28])[N:26]2[CH2:29][C@H:22]1[CH2:23][CH2:24][C@H:25]2[C:30]([O:32][CH2:34][CH:35]1[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]([CH3:45])([CH3:47])[CH3:46])=[O:42])[CH2:37][CH2:36]1)=[O:31])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 57389355(2S,5R)-6-(Benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid

Product 1

HCID 86659598HCID 86659598, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (109 mg, 0.57 mmol) and 4-dimethylaminopyridine (69.6 mg, 0.57 mmol) were added sequentially to a solution of (2S,5R)-6-(phenylmethoxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid (105 mg, 0.38 mmol) in dry dichloromethane at room temperature. tert-Butyl 4-(hydroxymethyl)piperidine-1-carboxylate (123 mg, 0.57 mmol) was then added and the reaction mixture was stirred at room temperature overnight, and then concentrated under vacuum. The residue was purified by preparative HPLC to afford the title compound.

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-cab5688cd3ec4ad696917bf5662ce052
Source dataset
uspto-grants-2013_07
Patent number
US08487093B2

Reaction notes

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