Dimethylformamide → HCID 86629182, compound

HRID 2421866Notes

Reaction equation

HRID 2421866 reaction equation
C(P(=O)(OCC)OCC)#N.[NH2:11][C:12]1[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=1[S:19][CH2:20][C@@H:21]([C:30]([OH:32])=O)[NH:22][O:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26].CN(C=O)C>CCOC(C)=O>[CH3:26][C:25]([CH3:28])([CH3:27])[C:24]([O:23][NH:22][C@@H:21]1[C:30](=[O:32])[NH:11][C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[S:19][CH2:20]1)=[O:29]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 76257Diethyl cyanophosphonateHCID 86629180HCID 86629180, compound

Product 1

HCID 86629182HCID 86629182, compoundYield 10.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

0.366 mL of diethyl cyanophosphonate (0.393 mg, 2.41 mmol) is placed in a 25 mL three-necked flask containing 670 mg of 49 (2.028 mmol) and 10 mL of DMF, at 0° C., followed by addition, after 10 minutes, of 0.273 mL of TEA (1.943 mmol). The reaction medium is stirred at 0° C. for 2 hours. 30 mL of EtOAc are added and the mixture is then washed with twice 30 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 (70 g) with a heptane/EtOAc eluent (as an EtOAc gradient: 8% to 50%). 68.4 mg of expected product 50 are obtained (white solid).

Workup

  1. washthe mixture is then washed with twice 30 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 (70 g) with a heptane/EtOAc eluent (as an EtOAc gradient

Sources & evidence

ORD record
ord-ef3bc3841c1649bb87d061a1321d39c3
Source dataset
uspto-grants-2011_06
Patent number
US07960373B2

Reaction notes

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