Hydrochloric Acid → ethyl 2-amino-3-hydroxypropanoate hydrochloride

HRID 325277Notes

Reaction equation

HRID 325277 reaction equation
[CH2:1]([O:8][C:9](=[O:23])[CH:10]([N:20]=[N+]=[N-])[CH2:11][O:12]CC1C=CC=CC=1)[C:2]1C=CC=CC=1.[ClH:24].[H][H]>C(O)C.[Pd]>[ClH:24].[CH2:1]([O:8][C:9](=[O:23])[CH:10]([CH2:11][OH:12])[NH2:20])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14104112HCID 14104112, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 2781220ethyl 2-amino-3-hydroxypropanoate hydrochlorideYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1.56 grams (0.005 mole) of 2-azido-3-benzyloxypropionic acid benzyl ester were dissolved in 10 ml of absolute ethanol, 1.10 grams (0.03 mole) of dry hydrogen chloride led in, and the mixture treated with 0.20 grams of palladium on activated carbon (10%). This reaction mixture was hydrogenated in an autoclave for 40 hours at 25° C., and a hydrogen pressure of 20 bar. After filtration, the filtrate was concentrated on the rotary evaporator, and the residue recrystallized from ethanol/diethyl ether (volume ratio about 1:1). There were obtained 0.81 grams (96% of theory) of D,L-serine ethyl ester hydrochloride having a melting point of 102°-103.5° C. (Literature: 100°-102° C.

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated on the rotary evaporator
  3. customthe residue recrystallized from ethanol/diethyl ether (volume ratio about 1:1)

Sources & evidence

ORD record
ord-5dbcc75165d84a198392ed6cc7d41162
Source dataset
uspto-grants-1984_04
Patent number
US04440686

Reaction notes

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