Triethylamine → HCID 178454243, compound

HRID 1430699Notes

Reaction equation

HRID 1430699 reaction equation
CCN(CC)CC.[C:8]([O:12][C:13](=[O:29])[N:14]=[C:15]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])N1C=CC=N1)([CH3:11])([CH3:10])[CH3:9].[NH2:30][CH2:31][C:32]1([C:35]2[O:39][C:38]([CH:40]3[CH2:46][CH2:45][C@@H:44]4[CH2:47][N:41]3[C:42](=[O:56])[N:43]4[O:48][CH2:49][C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[N:37][N:36]=2)[CH2:34][CH2:33]1>CO>[C:25]([O:24][C:22]([N:21]=[C:15]([NH:14][C:13]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:29])[NH:30][CH2:31][C:32]1([C:35]2[O:39][C:38]([CH:40]3[CH2:46][CH2:45][C@@H:44]4[CH2:47][N:41]3[C:42](=[O:56])[N:43]4[O:48][CH2:49][C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[N:37][N:36]=2)[CH2:33][CH2:34]1)=[O:23])([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4428040N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidineHCID 86701031(5R)-2-(5-(1-(aminomethyl)cyclopropyl)-1,3,4-oxadiazol-2-yl)-6-(benzyloxy)-1,6-diaza-bicyclo[3.2.1]octan-7-one

Product 1

HCID 178454243HCID 178454243, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Et3N (5 g, 0.05 mol) and tert-butyl(((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate (5.5 g, 17.5 mmol) were added to a solution of (5R)-2-(5-(1-(aminomethyl)cyclopropyl)-1,3,4-oxadiazol-2-yl)-6-(benzyloxy)-1,6-diaza-bicyclo[3.2.1]octan-7-one (7 g, 0.017 mol) in CH3OH (500 mL). The mixture was stirred at rt for 4 hrs and then concentrated. The residue was purified by silica gel column chromatography (gradient elution 50 to 66% EtOAc/petroleum ether) to afford (5R)-2-(5-(1-(2,3-bis-(tert-butoxycarbonyl)-guanidinomethyl)cyclopropyl)-1,3,4-oxadiazol-2-yl)-6-(benzyloxy)-1,6-diaza-bicyclo[3.2.1]octan-7-one (9 g, 86%) as a white solid. ESI-MS (EI+, m/z): 612.3 [M+H]+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by silica gel column chromatography (gradient elution 50 to 66% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-94e9f39f57ad419d86eebf16b740bb20
Source dataset
uspto-grants-2015_01
Patent number
US08940897B2

Reaction notes

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