Water → HCID 86726365, compound

HRID 629760Notes

Reaction equation

HRID 629760 reaction equation
[N:1]([C@@H:4]([C@H:40]([C:48]1[CH:53]=[CH:52][CH:51]=[C:50]([Cl:54])[CH:49]=1)[C:41]1[CH:46]=[CH:45][C:44]([F:47])=[CH:43][CH:42]=1)[C:5]([NH:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([F:39])[C:13]=1[CH2:14][CH2:15][C@H:16]1[O:21][CH2:20][C@H:19]([CH2:22][O:23][C:24]([NH:26][CH2:27][C:28]([F:31])([F:30])[F:29])=[O:25])[N:18]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:17]1)=[O:6])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[NH2:1][C@@H:4]([C@H:40]([C:48]1[CH:53]=[CH:52][CH:51]=[C:50]([Cl:54])[CH:49]=1)[C:41]1[CH:42]=[CH:43][C:44]([F:47])=[CH:45][CH:46]=1)[C:5]([NH:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([F:39])[C:13]=1[CH2:14][CH2:15][C@H:16]1[O:21][CH2:20][C@H:19]([CH2:22][O:23][C:24]([NH:26][CH2:27][C:28]([F:31])([F:29])[F:30])=[O:25])[N:18]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:17]1)=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86726366HCID 86726366, compound

Product 1

HCID 86726365HCID 86726365, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Step 2 (255 mg, 0.33 mmol) was dissolved in 3 mL THF and to the stirred solution was added triphenylphosphine (128 mg, 0.49 mmol) and water (0.3 mL). The mixture was heated to reflux for 24 h. The solvents were removed in vacuo and the residue was purified on a 12 g silica gel column eluting with a gradient of 0-30% EtOAc:hexanes. Fractions containing product were combined and the solvents were removed in vacuo to give a dense gum. LCMS: RT=1.23 min, M+H=756.5 (2 min gradient).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 24 h
  3. customThe solvents were removed in vacuo
  4. customthe residue was purified on a 12 g silica gel column
  5. washeluting with a gradient of 0-30% EtOAc
  6. additionFractions containing product
  7. customthe solvents were removed in vacuo
  8. customto give a dense gum
  9. customLCMS: RT=1.23 min, M+H=756.5 (2 min gradient)

Sources & evidence

ORD record
ord-d820b4da279d48469ccbdacf456e63fe
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

Loading…