Diisopropylethylamine → HCID 86701402, compound

HRID 870858Notes

Reaction equation

HRID 870858 reaction equation
CCN(C(C)C)C(C)C.[NH:10]([C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)=[S:13])[NH2:11].[CH2:27]([O:34][N:35]1[C:41](=[O:42])[N:40]2[CH2:43][C@H:36]1[CH2:37][CH2:38][C@H:39]2[C:44](O)=[O:45])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH2:27]([O:34][N:35]1[C:41](=[O:42])[N:40]2[CH2:43][C@H:36]1[CH2:37][CH2:38][C@H:39]2[C:44]([NH:11][NH:10][C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)=[S:13])=[O:45])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 45496782HCID 45496782, compoundHCID 57389355(2S,5R)-6-(Benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid

Product 1

HCID 86701402HCID 86701402, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIPEA (1.75 mL, 10.8 mmol) was added to a solution of tert-butyl 4-(hydrazinecarbonothioyl)piperazine-1-carboxylate (0.95 g, 3.6 mmol), (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carboxylic acid (1.0 g, 3.6 mmol) and HATU (1.51 g, 3.98 mmol) in dry DMF (15 mL) and the resulting reaction mixture was stirred at rt for 1 h. The reaction mixture was quenched with water (10 mL), and extracted with EtOAc (3×). The combined organic layer was dried over Na2SO4, then concentrated and purified by silica gel column chromatography (1:50 MeOH/DCM) to afford tert-butyl 4-(2-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)hydrazinecarbonothioyl)piperazine-1-carboxylate (0.92 g, 49%) as a light yellow solid. ESI-MS (EI+, m/z): 519.2 [M+H]+.

Workup

  1. customthe resulting reaction mixture
  2. customThe reaction mixture was quenched with water (10 mL)
  3. extractionextracted with EtOAc (3×)
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (1:50 MeOH/DCM)

Sources & evidence

ORD record
ord-6408b90540d24b54b010ca5903f720d0
Source dataset
uspto-grants-2015_03
Patent number
US08969570B2

Reaction notes

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