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 870853Notes

Reaction equation

HRID 870853 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-15098b4845d14544814f0a1d53d0fd17
Source dataset
uspto-grants-2015_03
Patent number
US08969570B2

Reaction notes

Loading…