Sodium hydride → HCID 89348460, compound

HRID 488527Notes

Reaction equation

HRID 488527 reaction equation
[C:1]1([P:7]([CH2:14][SH:15])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].CSNC(=O)C.[C:24]([NH:27][C@H:28]([C:36](O)=[O:37])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=[O:26])[CH3:25]>CN(C=O)C>[NH:27]([C:24]([CH3:25])=[O:26])[C@H:28]([C:36]([S:15][CH2:14][P:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:37])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 74839N-Acetyl-L-phenylalanineHCID 100435N-MethylmercaptoacetamideHCID 11230015(DIPHENYLPHOSPHINO)METHANETHIOL

Product 1

HCID 89348460HCID 89348460, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Method A (transthioesterification). Phosphinothiol 20 (500 mg, 2.2 mmol) was dissolved in dry TBF (5 mL). The solution was deoxygenated by bubbling Ar(g) for 0.5 h. To this solution was added NaH (51.6 mg, 2.2 mmol). The mixture formed a slurry to which was added DMF (2 mL0 to dissolve any precipitate. The N-methylmercaptoacetamide (NMA) thioester of N-acetylphenylalanine (63 mg, 0.22 mmol) was added, and the reaction mixture was stirred for 8 h. Unreacted Phosphinothiol 20 was removed by adding Merrifield resin (1.5 g, 1.26 mmol/g), stirring for 6 h, and removing the resin by filtration. The residue was purified by flash chromatography (silica gel, 50% ethyl acetate in hexanes). AcPheSCH2PPh2 was isolated as a white solid in 92% yield.

Workup

  1. customThe solution was deoxygenated
  2. customby bubbling Ar(g) for 0.5 h
  3. customThe mixture formed a slurry to which
  4. dissolutionto dissolve any precipitate
  5. customUnreacted Phosphinothiol 20 was removed
  6. additionby adding Merrifield resin (1.5 g, 1.26 mmol/g)
  7. stirringstirring for 6 h
  8. customremoving the resin
  9. filtrationby filtration
  10. customThe residue was purified by flash chromatography (silica gel, 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-d2edf7045dc54591938d7e7c3d47f087
Source dataset
uspto-grants-2005_12
Patent number
US06972320B2

Reaction notes

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