(Diethoxyphosphinyl)acetic acid → HCID 86756983, compound

HRID 1066032Notes

Reaction equation

HRID 1066032 reaction equation
[CH3:1]/[C:2](/[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:21])/[CH2:10][CH2:11]/[CH:12]=[C:13](\[CH3:20])/[CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])=[CH:3]\[CH2:4][NH2:5].[CH2:22]([O:24][P:25]([CH2:30][C:31](O)=[O:32])([O:27][CH2:28][CH3:29])=[O:26])[CH3:23].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C1COCC1>[O:32]=[C:31]([NH:5][CH2:4]/[CH:3]=[C:2](\[CH3:1])/[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:21])/[CH2:10][CH2:11]/[CH:12]=[C:13](\[CH3:20])/[CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])[CH2:30][P:25](=[O:26])([O:24][CH2:22][CH3:23])[O:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 36704(Diethoxyphosphinyl)acetic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13933000HCID 13933000, compound

Product 1

HCID 86756983HCID 86756983, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of compound 35 (0.360 g, 1.24 mmol), diethylphosphonoacetic acid (0.266 g, 1.36 mmol, prepared as disclosed by M. P. Cooke, K. B. Bicunas, Synthesis, 283, 1981, and 1-hydroxybenzotriazole (0.251 g, 1.86 mmol) in anhydrous THF (15 ml) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.285 g, 1.49 mmol). The mixture was stirred at rt for 24 h, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on 230-400 mesh silica gel (Macherey-Nagel Silica Gel 60 Art. Nr. 81538) eluting with CH2Cl2-hexane-MeOH (98:70:4) and collecting 4 mL fractions. The appropriate fractions were combined, evaporated, and pump-dried to give intermediate 36 (0.464 g, 80%) as an oil: 1H-NMR (CDCl3, 80 Mhz) δ 1.33 (t, 6H, J=7.1 Hz, 2×CH3CH2), 1.60 (s, 9H, 3×CH3), 1.67 (s, 6H, 2×CH3), 2.02 (m, 12H, 6×CH2), 2.83 (d, 2H, J=20 Hz, CH2P), 3.86 (d, 2H, J=7.1 Hz, CH2), 4.14 (q, 4H, J=7.1 Hz, 2×CH3CH2), 5.10 (br, 3H, 3×CH), 5.20 (t, 1H, J=7.1 Hz, CH); MS (FAB+) m/e 468 (M+H)+.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was purified by column chromatography on 230-400 mesh silica gel (Macherey-Nagel Silica Gel 60 Art. Nr. 81538)
  3. washeluting with CH2Cl2-hexane-MeOH (98:70:4)
  4. customcollecting 4 mL fractions
  5. customevaporated
  6. custompump-dried

Sources & evidence

ORD record
ord-4bf1968446054dafa3a93cb9281a33c9
Source dataset
uspto-grants-2001_06
Patent number
US06242433B1

Reaction notes

Loading…