p-Toluenesulfonic acid → HCID 18396424, compound

HRID 1768157Notes

Reaction equation

HRID 1768157 reaction equation
[C:1]1([CH3:11])[CH:6]=CC(S(O)(=O)=O)=CC=1.[NH2:12][C@H:13]([C:22]([O:24]CC=C)=O)[CH2:14][CH2:15][C:16]([O:18]CC=C)=[O:17].[CH3:28][C:29]1[CH:30]=CC(S(O)(=O)=O)=CC=1.N[C@H](C([O:51][CH2:52]C=C)=O)CCC(OCC=C)=O.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.C([N:69](CC)CC)C>C1(C)C=CC=CC=1>[CH2:28]([N:12]([CH2:11][CH:1]=[CH2:6])[C@H:13]([C:22]([N:69]=[C:52]=[O:51])=[O:24])[CH2:14][CH2:15][C:16](=[O:17])[OH:18])[CH:29]=[CH2:30]

Participants

7

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 94429TriphosgeneHCID 11053369diallyl L-glutamateHCID 1839642320845-16-3

Product 1

HCID 18396424HCID 18396424, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To diallyl L-glutamate p-toluene sulfonate (the TsOH salt of diallyl L-glutamate) (1.08 g, 2.7 mmol, NovaBiochem) and triphosgene (0.30 g, 1.03 mmol) in 20 mL toluene, stirred at −78° C., trietylamine (0.86 mL, 6.2 mmol) was added. After 30 min, the reaction mixture was allowed to reach room temperature and was used without further purification. A typical IR spectrum was obtained v=2253 cm−1 (NCO, v. intense).

Workup

  1. customto reach room temperature
  2. customwas used without further purification
  3. customA typical IR spectrum was obtained v=2253 cm−1 (NCO, v. intense)

Sources & evidence

ORD record
ord-d409cc13899c459d813458e7bb0cc81f
Source dataset
uspto-grants-2007_06
Patent number
US07235585B2

Reaction notes

Loading…