Triphenylphosphine → HCID 136347238, compound

HRID 601322Notes

Reaction equation

HRID 601322 reaction equation
[N:1]([CH2:4][C:5]1[C:13]2[S:12](=[O:15])(=[O:14])[N:11]=[C:10]([C:16]3[C:17](=[O:34])[N:18]([CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:19]4[C:24]([C:25]=3[OH:26])=[CH:23][CH:22]=[CH:21][CH:20]=4)[NH:9][C:8]=2[S:7][CH:6]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>N1C=CC=CC=1.[OH-].[NH4+]>[NH2:1][CH2:4][C:5]1[C:13]2[S:12](=[O:15])(=[O:14])[N:11]=[C:10]([C:16]3[C:17](=[O:34])[N:18]([CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:19]4[C:24]([C:25]=3[OH:26])=[CH:23][CH:22]=[CH:21][CH:20]=4)[NH:9][C:8]=2[S:7][CH:6]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 136358490HCID 136358490, compound

Product 1

HCID 136347238HCID 136347238, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 14923Ammonium HydroxideSolvent

Procedure

To the solution of the product of Example 344 (136.2 mg, 0.28 mmol) in pyridine (1.68 mL) and concentrated ammonium hydroxide (1.12 mL) was added triphenylphosphine (145 mg, 0.55 mmol) at room temperature. The solution was stirred at room temperature overnight and concentrated in vacuo. The residue was diluted with toluene and the solid was filtered to give the title compound as a light brown solid (100.78 mg, 78%). MS (ESI+) m/z 467 (M+H)+. 1H NMR (300 MHz, DMSO-d6) δ 4.10 (s, 2 H) 5.41 (br s, 2 H) 7.07-7.32 (m, 8 H) 7.43 (m, 1 H) 8.10 (dd, J=7.91, 1.65 Hz, 1 H).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with toluene
  3. filtrationthe solid was filtered

Sources & evidence

ORD record
ord-ef968bd7c6a04b25a909e880e83ddd10
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

Loading…