Diethyl chlorophosphate → HCID 131722626, compound

HRID 1066709Notes

Reaction equation

HRID 1066709 reaction equation
[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH2:28]([O:30][P:31](Cl)(=[O:35])[O:32][CH2:33][CH3:34])[CH3:29].[H-].[Na+]>O1CCOCC1>[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][P:31]([O:32][CH2:33][CH3:34])([O:30][CH2:28][CH3:29])=[O:35])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 13139Diethyl chlorophosphateHCID 24758Sodium hydrideHCID 7019055Boc-L-tyrosine benzyl ester

Product 1

HCID 131722626HCID 131722626, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared by reaction of BocTyrOBzl (371 mg, 1 mmol) and diethylphosphorochloridate (258 mg, 1.5 mmol) with an excess of NaH (60% in mineral oil) in dry dioxane for 3.5 h at 50° C. under argon atmosphere The solvent was concentrated in vacuo and the residue was dissolved in EtOAc and washed several times with a 5% solution of NaHCO3, a 10% solution of citric acid and a solution of satured NaCl. The organic phase was dried (Na2SO4) and concentrated, giving an oil 254 mg (50% yield), that was used without purification for the next step. FAB mass spectroscopy: m/z 508 [MH]+, 530 [MNa]+. H1NMR (200 Mhz, CDCl3) d (ppm)=7.4-6.85 (m, 9H, aromatics), 5.1 (d, 2H, COOCH2—F), 4.6 (m, 1H, N—CH—CO), 4.3-4 (m, 4H, P—O—CH2—CH3), 3 (t, 2H, CH—CH2—F), 1.4 (m, 15H, CH3− CH2+ tBu).

Workup

  1. concentrationwas concentrated in vacuo
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed several times with a 5% solution of NaHCO3
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-aecd11b4e14e44b590a971ebc0f5299b
Source dataset
uspto-grants-2001_06
Patent number
US06245742B1

Reaction notes

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