Carbon Dioxide → HCID 86584107, compound

HRID 2082589Notes

Reaction equation

HRID 2082589 reaction equation
[C:1](=[O:3])=O.Cl.[CH3:5][O:6][C:7](=[O:17])[C@H:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH2:9].C(N(CC)CC)C.P(Cl)(Cl)(Cl)=O>ClCCl.C(OCC)C>[N-:9]=[C:1]=[O:3].[CH3:5][O:6][C:7](=[O:17])[C@H:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH2:9]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 75736Methyl L-phenylalaninate hydrochloride

Product 1

HCID 86584107HCID 86584107, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

Carbon dioxide was added subsurface to a dichloromethane (20 mL) solution containing phenylalanine methylester hydrochloride salt (0.005 mol, 1.07 g), N-cyclohexyl-N',N',N",N"-tetraethylguanidine (0.005 mol, 1.3 g) and triethylamine (0.02 mol, 2.0 g) at -10° C. (ice and salt bath) for 30 min at a pressure of 0 psig. The reaction mixture was transferred rapidly via cannula under carbon dioxide to a pre-cooled solution of phosphorus oxychloride (0.005 mol, 0.8 g) in 20 mL dichloromethane. After stirring for 20 min at -10° C. diethylether (40 mL) was added to the reaction mixture. A white ppt. formed and was filtered off. The filtrate was concentrated in vacuo and the residue was extracted with 3×20 mL diethylether. The ether layers were concentrated and the residue distilled under vacuum (ca. 0.1-0.3 torr) collecting product, phenylalanine methyl ester isocyanate, at 91°-93° C. (0.426 g, 41.6%) of 93% purity as judged by GC. IR (neat) 2253, 1745 cm-1. 1H NMR (CDCl3) δ 7.35-7.17 (m, 5H), 4.26 (dd, 1H, Jgem =7.7, Jvic =4.7), 3.79 (s, 3H), 3.15 (dd, 2H, Jgem =13.8, Jvic =4.7), 3.01 (dd, 1H, Jgem =13.8, Jvic =7.8) ppm.

Workup

  1. additionwas added to the reaction mixture
  2. customformed
  3. filtrationwas filtered off
  4. concentrationThe filtrate was concentrated in vacuo
  5. extractionthe residue was extracted with 3×20 mL diethylether
  6. concentrationThe ether layers were concentrated
  7. distillationthe residue distilled under vacuum (ca. 0.1-0.3 torr)
  8. customcollecting product, phenylalanine methyl ester isocyanate
  9. customat 91°-93° C.

Sources & evidence

ORD record
ord-d967c37a6ddb43b8adb77cd75d786aff
Source dataset
uspto-grants-1993_02
Patent number
US05189205

Reaction notes

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