Hexafluorophosphate → HCID 18420299, compound

HRID 990256Notes

Reaction equation

HRID 990256 reaction equation
[O:1]=[C:2]([N:16]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:3]NC(=O)C1C=CC(C(=O)C)=CC=1.[C:31]([C:34]1[CH:42]=[CH:41][C:37]([C:38](O)=[O:39])=[CH:36][CH:35]=1)(=[O:33])[CH3:32].CC[N:45](C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[O:1]=[C:2]([N:16]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:3][C:41]1[CH:42]=[C:34]([C:31](=[O:33])[CH3:32])[CH:35]=[CH:36][C:37]=1[C:38]([NH2:45])=[O:39]

Participants

8

Reactant 5

HCID 9886HexafluorophosphateHCID 114704-Acetylbenzoic AcidHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 18369529HCID 18369529, compound

Product 1

HCID 18420299HCID 18420299, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-{2-Oxo-2-{di(phenylmethyl)amino}ethyl}-4-acetylbenzamide: To a solution of 4-acetylbenzoic acid (1.21 g, 7.37 mmol) in DMF (35 mL) was added successively the product of the preceding section (b) (2.03 g, 7.0 mmol), DIPEA (4.3 mL, 24.5 mmol) and BOP.PF6 (3.25 g, 7.37 mmol). The resulting solution was stirred at room temperature for 2 h, then diluted with EtOAc, washed serially with H2O, 4N aqueous HCl, saturated NaHCO3, and brine, dried (MgSO4) and concentrated under reduced pressure to give N {2-oxo-2-{di(phenylmethyl)amino}ethyl}-4-acetylbenzamide (2.70 g, 99% yield) as a light yellow foam: 1H NMR (400 MHz, DMSO-d6) 8 8.89 (t, 1H, J=5.7 Hz), 8.05 (d, 2H, J=8.4 Hz), 8.00 (d, 2H, J=8.4 Hz), 7.24-7.44 (m, 10 H), 4.61 (s, 2H), 4.51 (s, 2H), 4.25(d, 2H, J=5.7 Hz), 2.52 (s, 3H); MS (FAB) m/z 401 (MH)+. This product was used as such in the next reaction (section (d)).

Workup

  1. washwashed serially with H2O, 4N aqueous HCl, saturated NaHCO3, and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f0c8ac306c7a4094b4abb611f6139707
Source dataset
uspto-grants-2002_10
Patent number
US06458959B1

Reaction notes

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