Methanol → L-Phenylalanine, methyl ester

HRID 1805405Notes

Reaction equation

HRID 1805405 reaction equation
O=S(Cl)Cl.[NH2:5][C@H:6]([C:14]([OH:16])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:17]O>>[CH3:17][O:15][C:14](=[O:16])[C@H:6]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 6140L-PhenylalanineHCID 24386Thionyl Chloride

Product 1

HCID 736234L-Phenylalanine, methyl esterYield 88.3%

Procedure

6.61 mL of SOCl2 and 40 mL of methanol were thoroughly mixed in an ice bath for 30 minutes, followed by mixing with 10 g of L-phenylalanine. The mixture was subjected to a reflux reaction at 70° C. for 24 hours, followed by evaporating, re-crystallizing in ether, filtering and drying to obtain a product of 11.5 g (88.3%) of L-phenylalanine methyl ester 2. The analytic data of the product are as follows: 1H-NMR (D2O, 400 MHz), δ(ppm): 7.36-7.20 (m, 5H, Ar), 4.36-4.34 (t, 1H, J=6, H2NHCH), 3.75 (s, 3H, OCH3), 3.30-3.12 (m, 2H, CH2Ar); 13C-NMR (D2O, 100 MHz), δ(ppm): 170.2, 133.9, 129.5, 129.4, 129.3, 128.3, 128.1, 54.2, 53.7, 35.7; ESI-MS (m/z): calcd. 179.22, found 180.13 [M+H]+; Anal. Calcd (Found) for C10H13NO2.HCl: C, 55.69 (55.32); H, 6.45 (6.54); N, 6.49 (6.35).

Workup

  1. customThe mixture was subjected to a reflux reaction at 70° C. for 24 hours
  2. customby evaporating
  3. customre-crystallizing in ether
  4. filtrationfiltering
  5. customdrying

Sources & evidence

ORD record
ord-7f15df7e5deb41b796f5996dcf445195
Source dataset
uspto-grants-2013_01
Patent number
US08354512B2

Reaction notes

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