Dicyclohexylcarbodiimide → AcGlyCH2PPh2

HRID 488529Notes

Reaction equation

HRID 488529 reaction equation
[C:1]1([P:7]([CH2:14]S)[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.[C:16]([NH:19][CH2:20][C:21](O)=[O:22])(=[O:18])[CH3:17].C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[NH:19]([C:16]([CH3:17])=[O:18])[CH2:20][C:21]([CH2:14][P:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:22]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 10972AcetylglycineHCID 11230015(DIPHENYLPHOSPHINO)METHANETHIOL

Product 1

HCID 131725233AcGlyCH2PPh2Yield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phosphinothiol 20 (100 mg, 0.43 mmol) and N-acetylglycine (55 mg, 0.47 mmol) were dissolved in DMF (3 mL) under Ar(g). DCC (98 mg, 0.47 mmol) was added, and the mixture was stirred for 12 h at room temperature. The DCU by-product was removed by filtration, solvent was removed under reduced pressure, and the residue was purified by chromatography as in Method A. AcGlyCH2PPh2 was isolated as a white solid in 67% yield. Spectral data. 1H NMR (CDCl3, 300 MHz) δ 7.46-7.39 (m, 4 H), 7.38-7.36 (m, 6 H), 6.44 (bs, 1 H), 4.15 (d, J=5/7 Hz, 2 H), 3.53 (d, J=3.6 Hz, 2 H), 2.02 (s, 3 H) ppm; 13C NMR (CDCl3, 75 MHz) δ 196.13, 170.29, 136.45 (d, J=13.6 HZ), 132.62 (d, J=19.1 Hz), 129.17, 128.54 (d, J=6.7 Hz), 48.98, 25.29 (d, J-24.2 Hz), 22.84 ppm; 31P NMR (CDCl3, 121 MHz) δ −15.20 ppm; MS (ESI) m/z 331.08 (MH+—332.2, MK+—370.0).

Workup

  1. customThe DCU by-product was removed by filtration, solvent
  2. customwas removed under reduced pressure
  3. customthe residue was purified by chromatography as in Method A

Sources & evidence

ORD record
ord-0d5b9a23b5274aa49712eb2c61cce4fc
Source dataset
uspto-grants-2005_12
Patent number
US06972320B2

Reaction notes

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