Dimethylformamide → tert-butyl [(3S)-4-oxo-6-phenyl-2,3,4,5-tetrahydro-1,5-benzoxazepin-3-yl]carbamate

HRID 1670436Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

0.143 ml of diethyl cyanophosphonate (156 mg, 0.96 mmol) is introduced, at 0° C., into a 25 mL three-necked flask containing 260 mg of 42 (0.70 mmol) and 6.5 mL of DMF, followed 10 minutes later by 0.109 ml of TEA (0.77 mmol). The reaction medium is stirred at 0° C. for 2 h. 25 ml of AcOEt are added and then the mixture is washed with twice 25 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 (24 g, eluent heptane/AcOEt, in an AcOEt gradient: 25 to 75%). 85 mg of expected product 43 are obtained.

Workup

washthe mixture is washed with twice 25 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 (24 g, eluent heptane/AcOEt

Sources & evidence

ORD record: ord-e18bd6e060564230ad47c5143768aac6
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07994161B2

Reaction notes

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