Boc-Tyr-OMe → (S)-2-tert-Butoxycarbonylamino-3-[4-(2,3-dimethyl-pyridin-4-yloxy)-phenyl]-propionic acid methyl ester

HRID 879690

Reaction equation

HRID 879690 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C@@H:4]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[CH3:22][C:23]1[C:28]([CH3:29])=[C:27](B(O)O)[CH:26]=[CH:25][N:24]=1.O.CCOC(C)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:21])[C@@H:4]([NH:13][C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:27]2[CH:26]=[CH:25][N:24]=[C:23]([CH3:22])[C:28]=2[CH3:29])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 7019130Boc-Tyr-OMeHCID 22728543Water ethylacetateHCID 58327508(2,3-Dimethylpyridin-4-YL)boronic acid

Product 1

HCID 58327260(S)-2-tert-Butoxycarbonylamino-3-[4-(2,3-dimethyl-pyridin-4-yloxy)-phenyl]-propionic acid methyl esterYield 4.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 304 mg of (S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionic acid methyl ester, 314 mg 2,3-dimethylpyridine-4-boronic acid, 374 mg cupric acetate, and 2 grams of powdered 4 Å molecular sieves in 50 mL dry DCM and 0.75 mL TEA was stirred vigorously at rt under an O2 atmosphere for 40 h. The mixture was then poured into water-EtOAc. The organic layer was washed with water and saturated brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (DCM-EtOAc) to provide (S)-2-tert-Butoxycarbonylamino-3-[4-(2,3-dimethyl-pyridin-4-yloxy)-phenyl]-propionic acid methyl ester (18 mg). LCMS (m/z) 401.

Workup

  1. washThe organic layer was washed with water and saturated brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography (DCM-EtOAc)

Sources & evidence

ORD record
ord-37aeb88988e24c85973cd034d02c9e6a
Source dataset
uspto-grants-2015_03
Patent number
US08987295B2

Linked notes

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