Methanol → Phenylalanine, 4-chloro-, methyl ester

HRID 2390604Notes

Reaction equation

HRID 2390604 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][CH:7]([C:9]([OH:11])=[O:10])[NH2:8])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:18]O>>[CH3:18][O:10][C:9](=[O:11])[CH:7]([NH2:8])[CH2:6][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 4652FenclonineHCID 24386Thionyl Chloride

Product 1

HCID 26532Phenylalanine, 4-chloro-, methyl ester

Conditions

Temperature
0 °C

Procedure

4-Chloro-DL-phenylalanine (1.00 g, 5.00 mmol) was dissolved in methanol (30 mL) and cooled to 0° C. Thionyl chloride (2.92 mL, 40.0 mmol) was added dropwise. The mixture was allowed to warm to room temperature and was heated at reflux for 4 h. The solvent and reagents were removed in vacuo to yield the hydrochloride salt 1-1 as a white powder in quantitative yield (1.25 g, 5.00 mmol). 1H NMR (300 MHz, CD3OD): δ=7.37 (d, 2H, J=6.6 Hz), 7.27 (d, 2H, J=6.6 Hz), 4.34 (t, 1H, J=6.9 Hz), 3.81 (s, 3H), 3.26 (dd, 1H, J=14.4, 6.4 Hz), 3.18 (dd, 1H, J=14.4, 7.3 Hz); 13C NMR (75 mHz, CD3OD): δ=170.28, 134.87, 134.18, 132.11, 130.19, 54.99, 53.85, 38.81; ESI-MS calcd for C10H13ClNO2 [M+H]+: 214.0635. found 214.0638.

Workup

  1. temperatureto warm to room temperature
  2. temperaturewas heated
  3. temperatureat reflux for 4 h
  4. customThe solvent and reagents were removed in vacuo

Sources & evidence

ORD record
ord-5957c383ea2e49babd1950bdf7f9d3d9
Source dataset
uspto-grants-2012_09
Patent number
US08273778B2

Reaction notes

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