Dimethylformamide → HCID 86629176, compound

HRID 2421861Notes

Reaction equation

HRID 2421861 reaction equation
C(P(=O)(OCC)OCC)#N.[NH2:11][C:12]1[C:13]([S:24][CH2:25][C@@H:26]([C:35](O)=[O:36])[NH:27][O:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1.CN(C=O)C>CCOC(C)=O>[CH3:31][C:30]([CH3:32])([CH3:33])[C:29]([O:28][NH:27][C@@H:26]1[C:35](=[O:36])[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:13]=2[S:24][CH2:25]1)=[O:34]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 76257Diethyl cyanophosphonateHCID 86629174HCID 86629174, compound

Product 1

HCID 86629176HCID 86629176, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

0.269 mL of diethyl cyanophosphonate (289.4 mg, 1.774 mmol) are placed in a 25 mL three-necked flask containing 580 mg of 39 (1.493 mmol) and 7 mL of DMF, at 0° C., followed, 10 minutes later, by addition of 0.201 mL of TEA (1.43 mmol). The reaction medium is stirred at 0° C. for 2 hours. 20 mL of EtOAc are added and the mixture is then washed with twice 20 mL of distilled water. The organic phase is dried over MgSO4, filtered and then evaporated to dryness. The crude product (600 mg of yellow oil) is chromatographed on a silica cartridge (30 g) with a heptane/EtOAc eluent (as an EtOAc gradient: 10% to 50%). 410 mg of expected product 40 are obtained (white solid).

Workup

  1. washthe mixture is then washed with twice 20 mL of distilled water
  2. dry with materialThe organic phase is dried over MgSO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude product (600 mg of yellow oil) is chromatographed on a silica cartridge (30 g) with a heptane/EtOAc eluent (as an EtOAc gradient

Sources & evidence

ORD record
ord-ed855e8657dc49aeaa7fa8c766f0133e
Source dataset
uspto-grants-2011_06
Patent number
US07960373B2

Reaction notes

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