Water → HCID 86726369, compound

HRID 629762Notes

Reaction equation

HRID 629762 reaction equation
[N:1]([C@@H:4]([C@@H:40]([C:49]1[CH:54]=[CH:53][C:52]([Cl:55])=[CH:51][CH:50]=1)[C:41]1[CH:46]=[C:45]([F:47])[CH:44]=[C:43]([F:48])[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](=[O:31])[NH:25][CH2:26][C:27]([F:30])([F:29])[F:28])[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:49]1[CH:54]=[CH:53][C:52]([Cl:55])=[CH:51][CH:50]=1)[C:41]1[CH:42]=[C:43]([F:48])[CH:44]=[C:45]([F:47])[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](=[O:31])[NH:25][CH2:26][C:27]([F:30])([F:28])[F:29])[N:18]([C:32]([O:34][C:35]([CH3:36])([CH3:37])[CH3:38])=[O:33])[CH2:17]1)=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86726367HCID 86726367, compound

Product 1

HCID 86726369HCID 86726369, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from step 2 (150 mg, 0.19 mmol) and triphenylphosphine (74 mg, 0.28 mmol) were dissolved in THF (4 mL) and to the solution was added water (1 mL). The mixture was heated to reflux under a nitrogen atmosphere for 12 h. The mixture was cooled to ambient temperature and the solvents were removed in vacuo. The residue was purified on a 12 g silica gel column eluting with a gradient of 0-10% methanol:chloroform. Fractions containing product were combined and the solvents were removed in vacuo to give the title compound as a gum. (M+H)+=774.7.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under a nitrogen atmosphere for 12 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 0-10% methanol
  6. additionFractions containing product
  7. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-2d334ed81cc44584aaa11da7a550ce4f
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

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