Dimethylformamide → HCID 86629188, compound

HRID 2421874Notes

Reaction equation

C(P(=O)(OCC)OCC)#N.[NH2:11][C:12]1[C:17]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:16][CH:15]=[CH:14][C:13]=1[S:25][CH2:26][C@@H:27]([C:36](O)=[O:37])[NH:28][O:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32].CN(C=O)C>CCOC(C)=O>[CH3:34][C:31]([CH3:32])([CH3:33])[C:30]([O:29][NH:28][C@@H:27]1[C:36](=[O:37])[NH:11][C:12]2[C:17]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:16][CH:15]=[CH:14][C:13]=2[S:25][CH2:26]1)=[O:35]

Participants

Conditions

Temperature: 0 °C

Procedure

0.281 mL of diethyl cyanophosphonate (0.302 g, 1.85 mmol) is placed in a 25 mL three-necked flask containing 0.63 g of 59 (1.56 mmol) and 7.5 mL of DMF, at 0° C., followed by addition, after 10 minutes, of 0.21 mL of TEA (1.49 mmol). The reaction medium is stirred at 0° C. for 2 hours. 15 mL of EtOAc are added and the mixture is then washed with twice 15 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 (120 g) with a heptane/EtOAc eluent (as an EtOAc gradient: 0 to 30%). 188 mg of expected product 60 are obtained (white solid).

Workup

washthe mixture is then washed with twice 15 mL of distilled water
dry with materialThe organic phase is dried over MgSO4
filtrationfiltered
customevaporated to dryness
customThe crude product is chromatographed on a silica cartridge (120 g) with a heptane/EtOAc eluent (as an EtOAc gradient

Sources & evidence

ORD record: ord-fa28b4bc64474c3fb5bb2f447588be87
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960373B2

Reaction notes

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