Dimethylformamide → tert-butyl [(3S)-4-oxo-9-phenyl-2,3,4,5-tetrahydro-1,5-benzoxazepin-3-yl]carbamate

HRID 1670432Notes

Reaction equation

HRID 1670432 reaction equation
C(P(=O)(OCC)OCC)#N.[NH2:11][C:12]1[C:13]([O:24][CH2:25][C@@H:26]([C:35]([OH:37])=O)[NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[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>[O:37]=[C:35]1[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:13]=2[O:24][CH2:25][C@@H:26]1[NH:27][C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 76257Diethyl cyanophosphonateHCID 67328341O-(3-aminobiphenyl-2-yl)-N-(tert-butoxycarbonyl)-L-serine

Product 1

HCID 86628748tert-butyl [(3S)-4-oxo-9-phenyl-2,3,4,5-tetrahydro-1,5-benzoxazepin-3-yl]carbamateYield 59.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

0.136 ml of diethyl cyanophosphonate (147.8 mg, 0.906 mmol) is introduced, at 0° C., into a 25 mL three-necked flask containing 284 mg of 36 (0.763 mmol) and 6.2 mL of DMF, followed 10 minutes later by 0.102 ml of TEA (0.731 mmol). The reaction medium is stirred at 0° C. for 2 h. 20 ml of AcOEt are added and then the mixture is washed with twice 20 mL of distilled water. The organic phase is dried over MgSO4, filtered and then evaporated to dryness. 160 mg of expected product 37 are obtained.

Workup

  1. washthe mixture is washed with twice 20 mL of distilled water
  2. dry with materialThe organic phase is dried over MgSO4
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-2aab7ad252554f3d962913d91899c43d
Source dataset
uspto-grants-2011_08
Patent number
US07994161B2

Reaction notes

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