N-BOC-ethylenediamine → HCID 67121345, compound

HRID 333106Notes

Reaction equation

HRID 333106 reaction equation
O=C1CCC(=O)N1[O:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([O:21][CH2:22][CH:23]2[C:35]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:29]3[C:24]2=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:20])=[CH:14][CH:13]=1)=O.C([O-])(O)=O.[Na+].[C:41]([NH:48][CH2:49][CH2:50][NH2:51])([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42]>O.CC#N>[C:44]([O:43][C:41]([NH:48][CH2:49][CH2:50][NH:51][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([O:21][CH2:22][CH:23]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=3[C:30]3[C:35]2=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:20])=[CH:14][CH:13]=1)=[O:8])=[O:42])([CH3:45])([CH3:46])[CH3:47]

Participants

5

Reactant 3

HCID 187201N-BOC-ethylenediamineHCID 516892Sodium BicarbonateHCID 87276995HCID 87276995, compound

Product 1

HCID 67121345HCID 67121345, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A solution of N-{4-[(2,5-dioxoazolidinyloxy)carbonylamino]phenyl}(fluoren-9-ylmethoxy)carboxamide (16.10 g, 34.15 mmol, 1.0 eq) in H2O/CH3CN (1/1, v/v, 360 mL) is reacted at room temperature with NaHCO3 (2.86 g, 34.15 mmol, 1.0 eq) and N—BOC-ethylenediamine (5.47 g, 34.15 mmol, 1.0 eq). After stirring overnight at room temperature, the reaction mixture is filtered to afford 16.36 g of the expected crude product as a white solid.

Workup

  1. filtrationthe reaction mixture is filtered

Sources & evidence

ORD record
ord-ca1c218665b04b40b55244ce72dc0ef9
Source dataset
uspto-grants-2014_11
Patent number
US08877961B2

Reaction notes

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