Dimethylformamide → HCID 86629185, compound

HRID 2421870Notes

Reaction equation

HRID 2421870 reaction equation
C(P(=O)(OCC)OCC)#N.[NH2:11][C:12]1[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:13]=1[S:20][CH2:21][C@@H:22]([C:31]([OH:33])=O)[NH:23][O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27].CN(C=O)C>CCOC(C)=O>[CH3:27][C:26]([CH3:29])([CH3:28])[C:25]([O:24][NH:23][C@@H:22]1[C:31](=[O:33])[NH:11][C:12]2[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:13]=2[S:20][CH2:21]1)=[O:30]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 76257Diethyl cyanophosphonateHCID 86629183HCID 86629183, compound

Product 1

HCID 86629185HCID 86629185, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

0.948 mL of diethyl cyanophosphonate (1.019 g, 6.245 mmol) is placed in a 100 mL three-necked flask containing 1.80 g of 54 (5.26 mmol) and 25 mL of DMF, at 0° C., followed by addition, after 10 minutes, of 0.708 mL of TEA (5.04 mmol). The reaction medium is stirred at 0° C. for 2 hours. 50 mL of EtOAc are added and the mixture is then washed with twice 50 mL of distilled water. The organic phase is dried over MgSO4, filtered and then evaporated to dryness. The crude product is chromatographed on a silica cartridge (150 g) eluting with heptane/EtOAc (as an EtOAc gradient: 10% to 50%). 450 mg of expected product 55 are obtained (white solid).

Workup

  1. washthe mixture is then washed with twice 50 mL of distilled water
  2. dry with materialThe organic phase is dried over MgSO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude product is chromatographed on a silica cartridge (150 g)
  6. washeluting with heptane/EtOAc (as an EtOAc gradient

Sources & evidence

ORD record
ord-f1af75ac237a4f4ca8f73fa0a438ac33
Source dataset
uspto-grants-2011_06
Patent number
US07960373B2

Reaction notes

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