Ammonia → HCID 16226288, compound

HRID 1517628Notes

Reaction equation

HRID 1517628 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C@H:10]([NH:14][C:15]([NH:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=1[CH:20]=[N:21][N:22]3[C:27]([O:29][CH2:30][CH2:31][CH2:32][O:33][P:34]([O:41]C(C)(C)C)([O:36]C(C)(C)C)=[O:35])=[O:28])=[O:16])[CH2:9][CH2:8]2)([CH3:4])([CH3:3])[CH3:2].C(#N)C.FC(F)(F)C(O)=O.N>O>[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C@H:10]([NH:14][C:15]([NH:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=1[CH:20]=[N:21][N:22]3[C:27]([O:29][CH2:30][CH2:31][CH2:32][O:33][P:34]([OH:36])([OH:41])=[O:35])=[O:28])=[O:16])[CH2:9][CH2:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6342AcetonitrileHCID 6422Trifluoroacetic acid2×HCID 69450017HCID 69450017, compound

Product 1

HCID 16226288HCID 16226288, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the product from Example 15D (2.12 g, 3.30 mmol) in a 250 ml round bottom flask was added acetonitrile (40 ml) and 0.1% trifluoroacetic acid in water (40 ml) and the reaction was stirred at room temperature for 4 days. Every 24 hours 0.5 ml of trifluoroacetic acid was added until day four. The reaction was concentrated to give a white powder in 81% yield. 1H NMR (CDCl3, 300 MHz); δ ppm 1.32 (s, 9H), 1.88-1.92 (m, 1H), 2.22-2.26 (m, 2H), 2.57-2.63 (m, 1H), 2.84-2.90 (m, 1H), 2.96-3.32 (m, 1H), 4.21 (m, 2H), 4.65 (t, J=6.11, 12.55Hz, 2H), 5.29 (t, J=7.46, 14.58 Hz, 1H), 7.28-7.31 (m, 3H), 7.52 (t, J=8.14, 16.28 Hz, 1H), 7.73 (d, J=7.45Hz, 1H), 7.83 (d, J=8.48Hz, 1H), 8.36 (s, 1H); MS (DCI/NH3) m/z 531.00; Calc for C25H31N4O7P: C, 54.45; H, 5.59; N, 9.92. Found: C, 54.84; H, 5.88; N, 9.92.

Workup

  1. concentrationThe reaction was concentrated
  2. customto give a white powder in 81% yield

Sources & evidence

ORD record
ord-2d5f748723364f8c8de6f7122088106c
Source dataset
uspto-grants-2012_07
Patent number
US08232309B2

Reaction notes

Loading…