p-Toluenesulfonic acid monohydrate → N-[(Phenylmethoxy)carbonyl]-L-tyrosine methyl ester

HRID 1698930

Reaktionsgleichung

Reaktionsgleichung von HRID 1698930
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([NH:13][C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.O.[C:25]1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C(Cl)Cl>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C@H:9]([NH:13][C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])[C:10]([O:12][CH3:25])=[O:11])=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 712438N-benzyloxycarbonyl-l-tyrosine

Produkt 1

HCID 7010613N-[(Phenylmethoxy)carbonyl]-L-tyrosine methyl esterAusbeute 96,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 15.6 g (49 mmol) (2S)-3-(4-hydroxyphenyl)-2-[(phenylmethoxy)carbonylamino]propanoic acid in 120 mL methanol was added 9.4 g (49 mmol) of p-toluenesulfonic acid monohydrate. The solution was heated to 70 ° C. for 2 h. After solution was cooled to room temperature, the methanol was removed under reduced pressure. The solid obtained was redissolved in 120 mL methylene chloride. The organic solution was then washed with dilute NaHCO3 solution twice and brine. The organic layer was dried with anhydrous MgSO4 and filtered. The solvent was removed under reduced pressure. The crude mixture was chromatographed on a silica gel column using 40% ethyl acetate in hexanes as the eluent to yield 15.6 g (96%) of white solid as product: 1H NMR (300 MHz, CDCl3) δ7.38-7.30 (m, 5H), 6.93 (d, J=8.41 Hz, 2H), 6.81 (d, J=8.41 Hz, 2H), 5.39 (br s, 1H), 5.24 (d, J=9.29 Hz, 1H), 5.11 (d, J=12.32 Hz, 1H), 5.06 (d, J=12.29 Hz, 1H), 4.61 (m, 1H), 3.71 (s, 3H), 3.06 (dd, J=5.88, 14.06 Hz, 1H), 2.98 (dd, J=5.88, 14.06 Hz, 1H)

Aufarbeitung

  1. temperatureAfter solution was cooled to room temperature
  2. customthe methanol was removed under reduced pressure
  3. customThe solid obtained
  4. washThe organic solution was then washed with dilute NaHCO3 solution twice
  5. dry with materialThe organic layer was dried with anhydrous MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure
  8. customThe crude mixture was chromatographed on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-708ded514bd64b18b1a7d9b4fbd38ad3
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06344484B1

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