Methanol → (R)-Methyl 2-aminopent-4-enoate hydrochloride

HRID 37766Notes

Reaction equation

HRID 37766 reaction equation
[NH2:1][C@H:2]([CH2:6][CH:7]=[CH2:8])[C:3]([OH:5])=[O:4].S(Cl)([Cl:11])=O.[CH3:13]O>>[ClH:11].[NH2:1][C@H:2]([CH2:6][CH:7]=[CH2:8])[C:3]([O:5][CH3:13])=[O:4]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 6992334D-Allylglycine

Product 1

HCID 11446532(R)-Methyl 2-aminopent-4-enoate hydrochlorideYield 100%

Procedure

To a suspension of (2R)-2-amino-4-pentenoic acid (200 mg, 1.74 mmol) in methanol (6 mL) at 0° C. was added dropwise thionyl chloride (1 mL). The resulting solution was allowed to stir for 16 h before the solvent was removed by evaporation and the product crystallized with diethyl ether. The diethyl ether was removed by evaporation to yield the title compound (287 mg, 1.74 mmol, 100%) as a white solid which had spectral data in agreement with that reported.123 Mp 135-140° C. 1H NMR (CDCl3, 300 MHz): δ 8.70 (bs, 3H, NH3′); 5.89 (m, 1H, H4); 5.32 (d, J=17.3 Hz, 1H, H5a); 5.24 (d, J=10.1 Hz, 1H, H5b); 4.31 (m, 1H, H2); 3.81 (s, 3H, OCH3); 2.87 (t, J=6.3 Hz, 2H, H3). Mass Spectrum (ES, +ve) m/z 130 (100%) [M+]. HRMS calcd for C6H12NO2 130.0868, found 130.0870.

Workup

  1. customwas removed by evaporation
  2. customthe product crystallized with diethyl ether
  3. customThe diethyl ether was removed by evaporation

Sources & evidence

ORD record
ord-10deba963c2b4ec3bb5960a884ad0927
Source dataset
uspto-grants-2013_09
Patent number
US08524657B2

Reaction notes

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