Sodium Carbonate → Boc-4-(3-pyridyl)phenylalanine methyl ester

HRID 1530935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1530935
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17](I)=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C(=O)([O-])[O-].[Na+].[Na+].C(B(CC)[C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1)C>C(COC)OC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 6428513-(Diethylboryl)pyridineHCID 10319078N-Boc-4-iodophenylalanine methylester

Produkt 1

HCID 15379602Boc-4-(3-pyridyl)phenylalanine methyl esterAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture of N-Boc-4-iodo-L-phenylalanine methyl ester (810 mg, 2 mmol, Lei, H et al, ibid) tetrakis(triphenylphosphine)palladium (0) (231 mg, 0.2 mmol), aqueous sodium carbonate (4 mmol, 2 ml of a 2M solution) and diethyl(3-pyridyl)borane (294 mg, 2 mmol) in dimethoxyethane (30 ml) was refluxed for 6 hr. The solvent was removed in vacuo, the residue dissolved in EtOAc (100 ml) and washed with water (30 ml) aqueous sodium thiosulphate (20 ml) and brine (30 ml) dried (Na2SO4)and evaporated in vacuo. Purification by column chromatography (SiO2, EtOAc/hexane 30:70) gave the title compound (335 mg,47%) as a yellow oil. δH (CDCl3) 8.81 (1 H, d, J 1.7 Hz, PyrH), 8.56 (1 H, dd, J 4.8, 1.6 Hz, PyrH), 7.84 (1 H, dt, J 7.9, 2.0 Hz, PyrH), 7.49 (2 H, d, J 8.2 Hz, ArH), 7.34 (1 H, ddd, J 7.9, 4.8, 0.6 Hz, PyrH), 7.23 (2 H, d, J 8.2 Hz, ArH), 5.09 (1 H, br d, J 7.8 Hz, CONH), 4.62 (1 H, br q, J 6.8 Hz, CHα), 3.73 (3 H, s, CO2Me), 3.18 (1 H, dd, J 13.8, 5.6 Hz, CHAHBAr), 3.07 (1 H, dd, J 13.8, 5.8 Hz, CHAHBAr) and 1.40 (9 H, s, tBu); m/z (ESI, 15 V) 357 (MH+).

Aufarbeitung

  1. temperaturewas refluxed for 6 hr
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in EtOAc (100 ml)
  4. washwashed with water (30 ml) aqueous sodium thiosulphate (20 ml) and brine (30 ml) dried (Na2SO4)and
  5. customevaporated in vacuo
  6. customPurification by column chromatography (SiO2, EtOAc/hexane 30:70)

Quellen und Nachweise

ORD-Eintrag
ord-74e0886f6f5149fa8dc319aded37deff
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06197794B1

Notizen zur Reaktion

Wird geladen…