Triphenylphosphine → HCID 86605359, compound

HRID 132526Notes

Reaction equation

HRID 132526 reaction equation
[CH:1]([O:4][P:5]([CH2:11][O:12][CH2:13][N:14]1[C:22]([CH2:23][CH2:24][CH2:25][N:26]=[N+]=[N-])=[N:21][C:20]2[C:15]1=[N:16][C:17]([C:32]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[N:18][C:19]=2[NH:29][O:30][CH3:31])([O:7][CH:8]([CH3:10])[CH3:9])=[O:6])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[CH:8]([O:7][P:5]([CH2:11][O:12][CH2:13][N:14]1[C:22]([CH2:23][CH2:24][CH2:25][NH2:26])=[N:21][C:20]2[C:15]1=[N:16][C:17]([C:32]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)([C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)=[N:18][C:19]=2[NH:29][O:30][CH3:31])([O:4][CH:1]([CH3:3])[CH3:2])=[O:6])([CH3:9])[CH3:10]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 86605358HCID 86605358, compound

Product 1

HCID 86605359HCID 86605359, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 38 (805 mg, 1.15 mmol) in THF (8 mL) and water (1.6 mL) is treated with triphenylphosphine (640 mg, 2.44 mmol) and stirred at room temperature for 14 h. The reaction mixture is concentrated and purified on silica gel column using chloroform:CMA-80 (1:0 to 1:1) as eluent to give 660 mg (85%) as a white solid: 1H NMR (DMSO-d6): δ 8.09 (s, 1H), 7.72 (s, 1H), 7.17-7.00 (m, 13H), 6.67 (d, J=9.0 Hz, 2H), 4.70-4.59 (m, 1H), 4.28-4.16 (m, 2H), 3.95 (t, J=9.2 Hz, 1H), 3.68-3.45 (m, 3H), 3.54 (s, 3H), 2.29-2.05 (m, 2H), 1.93-1.60 (m, 4H), 0.96-0.91 (m, 6H), 0.84 (d, J=6.1 Hz, 6H). IR (neat, cm−1) 3414, 3020, 1605, 1511 and 1216. Anal. Calcd for C36H45N6O5P.1.5 H2O: C, 61.79; H, 6.91; N, 12.01. Found: C, 61.70; H, 6.63; N, 12.07.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. custompurified on silica gel column
  3. customCMA-80 (1:0 to 1:1) as eluent to give 660 mg (85%) as a white solid

Sources & evidence

ORD record
ord-3f0d1a2c7e714e2b8e43b044f2034070
Source dataset
uspto-grants-2008_06
Patent number
US07388002B2

Reaction notes

Loading…