Trimethyl phosphite → HCID 136375590, compound

HRID 2250149Notes

Reaction equation

HRID 2250149 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]3[NH:14][C:13]([C:15]([C:51]4[C:56]([CH3:57])=[CH:55][C:54]([CH3:58])=[CH:53][C:52]=4[CH3:59])=[C:16]4[N:50]=[C:19]([C:20]([C:41]5[C:46]([CH3:47])=[CH:45][C:44]([CH3:48])=[CH:43][C:42]=5[CH3:49])=[C:21]5[NH:40][C:24](=[C:25]([C:31]6[C:36]([CH3:37])=[CH:35][C:34]([CH3:38])=[CH:33][C:32]=6[CH3:39])[C:26]6[CH:27]=[CH:28][C:29]=2[N:30]=6)[CH:23]=[CH:22]5)[CH:18]=[CH:17]4)=[CH:12][CH:11]=3)=[CH:5][CH:4]=1.[CH3:60][O:61][P:62]([O:65]C)[O:63][CH3:64]>C1(C)C=CC=CC=1>[CH3:60][O:61][P:62]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]3[NH:14][C:13]([C:15]([C:51]4[C:56]([CH3:57])=[CH:55][C:54]([CH3:58])=[CH:53][C:52]=4[CH3:59])=[C:16]4[N:50]=[C:19]([C:20]([C:41]5[C:46]([CH3:47])=[CH:45][C:44]([CH3:48])=[CH:43][C:42]=5[CH3:49])=[C:21]5[NH:40][C:24](=[C:25]([C:31]6[C:36]([CH3:37])=[CH:35][C:34]([CH3:38])=[CH:33][C:32]=6[CH3:39])[C:26]6[CH:27]=[CH:28][C:29]=2[N:30]=6)[CH:23]=[CH:22]5)[CH:18]=[CH:17]4)=[CH:12][CH:11]=3)=[CH:5][CH:4]=1)([O:63][CH3:64])=[O:65]

Participants

4

Reactant 2

HCID 8472Trimethyl phosphiteHCID 136076361HCID 136076361, compound

Product 1

HCID 136375590HCID 136375590, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 26 (200 mg, 240 μmol) in trimethylphosphite (2.2 mL) and toluene (5 mL) was heated to 120° C. under argon for 17 h. The reaction mixture was cooled and concentrated under vacuum. The residue was chromatographed [silica, CHCl3→CHCl3/ethyl acetate (95:5)] to afford a purple solid (164 mg, 79%): 1H NMR δ-2.57 (br s, 2H), 1.84-1.85 (m, 18H), 2.62 (s, 9H), 3.50 (d, J=21.6 Hz, 2H), 3.87 (d, J=11.1 Hz, 6H), 7.27 (s, 6H), 7.67 (dd, J1=8.4 Hz, J2=1.8 Hz, 2H), 8.15 (d, J=7.8 Hz, 2H), 8.63 (s, 4H), 8.67 (d, J=4.8 Hz, 2H), 8.75 (d, J=4.8 Hz, 2H); 31P NMR δ 29.50; LDMS obsd 863.2; FABMS obsd 862.4045; calcd 862.4012 (C56H55N4O3P); λabs=421, 514, 547, 593, 649 nm.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under vacuum
  3. customThe residue was chromatographed [silica, CHCl3→CHCl3/ethyl acetate (95:5)]

Sources & evidence

ORD record
ord-c47e0654790444db9dbcd7cdf884b677
Source dataset
uspto-grants-2008_01
Patent number
US07314941B2

Reaction notes

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