Phosphoric Acid → N-carbomethoxy-L-alanine

HRID 1914457Notes

Reaction equation

HRID 1914457 reaction equation
[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].[OH-].[Na+].Cl[C:10]([O:12][CH3:13])=[O:11].P(=O)(O)(O)O>>[CH3:13][O:12][C:10]([NH:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3])=[O:11]

Participants

5

Reactant 4

HCID 1004Phosphoric AcidHCID 5950L-AlanineHCID 6586Methyl chloroformateHCID 14798Sodium Hydroxide2×

Product 1

HCID 13048344N-carbomethoxy-L-alanineYield 78%

Conditions

Temperature
0 °C

Procedure

To a stirred solution of L-alanine (300 g, 3.37 mol sodium hydroxide (1N, 1800 cm3) at 0° C. in an ice bath was added dropwise, over 2 hours, methyl chloroformate (274 cm3, 3.54 mol). The pH of the solution was maintained at 9 by the addition of sodium hydroxide (5N). The reaction mixture was stirred at 0° C. for 3 hours whereupon it was acidified to pH 1 by the addition of phosphoric acid solution (15%) and extracted with diethyl ether (5×1000 cm3). The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure to yield the product as a viscous green oil (386 g, 78%). 1H NMR (250 MHz; C2HCl3) 1.48 (3H, d, J7.25, CH3), 3.72 (3H, s, COCH3), 4.40 (1H, quintet, J7.25, CH), 5.31 (1H, bs, NH).

Workup

  1. extractionextracted with diethyl ether (5×1000 cm3)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-80d3d631989d4837ac960fbe4366ecb3
Source dataset
uspto-grants-2013_12
Patent number
US08613948B2

Reaction notes

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