Triethyl phosphite → HCID 87849905, compound

HRID 339610Notes

Reaction equation

HRID 339610 reaction equation
[C:1]([O:9][C@H:10]1[C@H:14]([F:15])[C@H:13]([N:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:18][C:17]2=[O:31])[O:12][C@@H:11]1[CH2:32]Br)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[P:34]([O:41]CC)([O:38][CH2:39][CH3:40])[O:35][CH2:36][CH3:37]>>[C:1]([O:9][C@H:10]1[C@H:14]([F:15])[C@H:13]([N:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:18][C:17]2=[O:31])[O:12][C@@H:11]1[CH2:32][P:34]([O:38][CH2:39][CH3:40])([O:35][CH2:36][CH3:37])=[O:41])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 69475736HCID 69475736, compound

Product 1

HCID 87849905HCID 87849905, compoundYield 44%

Procedure

A solution of compound 4 (0.08 g, 0.16 mmol) in 10 mL of (EtO)3P was stirred at 140° C. for 24 h and the solvent was evaporated under reduced pressure. The residue was dissolved in 10 mL of MeOH and adsorbed on silica gel and then purified on silica gel column chromatography (Hexane:EtOAc=1:2 to 1:4 v/v) to give compound 5 (0.04 g, 0.07 mmol) in 44% yield. 1H NMR (CDCl3, 400 MHz) δ 8.97 (br, 1H), 8.08 (d, J=7.2, 2H), 8.04 (d, J=7.6, 1H), 7.92 (d, J=7.2, 2H), 7.60 (m, 3H), 7.50 (m, 4H), 5.98 (d, J=18.4, 1H), 5.65 (d, J=4.8, 0.5H), 5.52 (d, J=4.8, 0.5H), 5.45 (m, 1H), 4.76 (m, 1H), 4.11 (m, 4H), 2.42 (m, 2H), 1.32 (m, 6H); MS calcd for C27H29FN3O8P m/z 574.2 (M+H)+, found 574.3.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in 10 mL of MeOH
  3. custompurified on silica gel column chromatography (Hexane:EtOAc=1:2 to 1:4 v/v)

Sources & evidence

ORD record
ord-21f7c24fe8574c8399e6ec8457a69977
Source dataset
uspto-grants-2014_11
Patent number
US08895531B2

Reaction notes

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