Oxamic Acid → HCID 86701011, compound

HRID 1430680Notes

Reaction equation

HRID 1430680 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:25]([O:32][N:33]1[C:39](=[O:40])[N:38]2[CH2:41][C@H:34]1[CH2:35][CH2:36][C@H:37]2[C:42]([NH:44][NH2:45])=[O:43])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[NH2:46][C:47](=[O:51])[C:48](O)=[O:49].CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:25]([O:32][N:33]1[C:39](=[O:40])[N:38]2[CH2:41][C@H:34]1[CH2:35][CH2:36][C@H:37]2[C:42]([NH:44][NH:45][C:48](=[O:49])[C:47]([NH2:46])=[O:51])=[O:43])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 974Oxamic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86701012HCID 86701012, compound

Product 1

HCID 86701011HCID 86701011, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

HATU (0.95 g, 2.5 mmol) was added to a 0° C. solution of (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide (1.00 g, 2.5 mmol), 2-amino-2-oxoacetic acid (0.18 g, 2.1 mmol) and DIPEA (1.08 g, 8.4 mmol) in DMF (10 mL). The reaction mixture was stirred at 0° C. for 1 h then quenched with saturated sodium chloride (50 mL) and the organic layer was separated. The aqueous layer was exacted with EtOAc (3×). The combined organic layer was washed with saturated sodium chloride (2×), dried over Na2SO4, and concentrated. The residue was purified by silica gel column chromatography (1:1 EtOAc/hexane) to give 2-(2-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbonyl)hydrazinyl)-2-oxoacetamide (0.57 g, 64%). ESI-MS (EI+, m/z): 362 [M+H]+.

Workup

  1. customthen quenched with saturated sodium chloride (50 mL)
  2. customthe organic layer was separated
  3. washThe combined organic layer was washed with saturated sodium chloride (2×)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (1:1 EtOAc/hexane)

Sources & evidence

ORD record
ord-8c5ae3a237794119a34dc8b4bca8c0a8
Source dataset
uspto-grants-2015_01
Patent number
US08940897B2

Reaction notes

Loading…