Phosphorus pentachloride → 17136-54-8

HRID 443474Notes

Reaction equation

HRID 443474 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[ClH:7].[CH3:8][O:9][C:10](=[O:15])[C@H:11]([CH2:13]O)[NH2:12]>C(Cl)Cl>[ClH:2].[CH3:8][O:9][C:10](=[O:15])[C@H:11]([CH2:13][Cl:7])[NH2:12]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

Product 1

HCID 1775087517136-54-8Yield 90.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 104 g of phosphorous pentachloride in 550 ml of methylene chloride at -10° C., is added 70 g of L-serine methyl ester hydrochloride, in approximately 5 g portions, over a period of 40 minutes while the temperature is maintained between -10 and 0° C. The reaction mixture is then allowed to warm to room temperature with stirring. Stirring is continued for 2-3 hours and the mixture is then poured into 550 ml of stirred petroleum ether. The resultant mixture is filtered and the filter cake is washed with petroleum ether (3×100 ml) and then with ether (2×100 ml). The combined filtrate and washings are dried under vacuum over sodium hydroxide pellets to afford 71 g of β-chloroalanine methyl ester hydrochloride.

Workup

  1. temperaturein approximately 5 g portions, over a period of 40 minutes while the temperature is maintained between -10 and 0° C
  2. stirringStirring
  3. filtrationThe resultant mixture is filtered
  4. washthe filter cake is washed with petroleum ether (3×100 ml)
  5. dry with materialThe combined filtrate and washings are dried under vacuum over sodium hydroxide pellets

Sources & evidence

ORD record
ord-6348d90b04764ca1a608e0e4470e9452
Source dataset
uspto-grants-1981_04
Patent number
US04260681

Reaction notes

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