Diisopropylethylamine → tert-butyl (2-(2-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbonyl)hydrazinyl)-2-oxoethyl)carbamate

HRID 515625Notes

Reaction equation

HRID 515625 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:25]([C:27](=[O:37])[CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[NH2:26].[CH2:38]([O:45][N:46]1[C:52](=[O:53])[N:51]2[CH2:54][C@H:47]1[CH2:48][CH2:49][C@H:50]2[C:55](O)=[O:56])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:38]([O:45][N:46]1[C:52](=[O:53])[N:51]2[CH2:54][C@H:47]1[CH2:48][CH2:49][C@H:50]2[C:55]([NH:26][NH:25][C:27](=[O:37])[CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:56])[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2735639tert-butyl N-[(hydrazinecarbonyl)methyl]carbamateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57389355(2S,5R)-6-(Benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid

Product 1

HCID 86701397tert-butyl (2-(2-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbonyl)hydrazinyl)-2-oxoethyl)carbamateYield 72.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

HATU (4.9 g, 12.9 mmol) and tert-butyl 2-hydrazinyl-2-oxoethylcarbamate (2.2 g, 11.4 mmol) were added to a solution of (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carboxylic acid (3 g, 10.8 mmol) in CH2Cl2 (50 mL) at 0° C. DIPEA (4.2 g, 32.6 mmol) was then added and the reaction mixture was stirred at 0° C. for 12 hrs. The reaction mixture was then washed with water, and saturated sodium chloride, dried over Na2SO4, and concentrated. The crude sample was purified by silica gel column chromatography (1 to 10% MeOH/DCM) to give tert-butyl (2-(2-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbonyl)hydrazinyl)-2-oxoethyl)carbamate (3.5 g, 62%) as a white solid. ESI-MS (EI+, m/z): 448.2 [M+H]+.

Workup

  1. washThe reaction mixture was then washed with water, and saturated sodium chloride
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude sample was purified by silica gel column chromatography (1 to 10% MeOH/DCM)

Sources & evidence

ORD record
ord-9414864734834a6cb04556798ce2acff
Source dataset
uspto-grants-2015_08
Patent number
US09108966B2

Reaction notes

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