Diisopropylethylamine → (S)-2-tert-Butoxycarbonylamino-3-[4-(3-cyano[1,6]naphthyridin-2-ylamino)phenyl]propionic acid methyl ester

HRID 852241Notes

Reaction equation

HRID 852241 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]([NH2:12])=[CH:8][CH:7]=1.Cl[C:23]1[C:32]([C:33]#[N:34])=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[N:28][CH:29]=2)[N:24]=1.C(N(C(C)C)CC)(C)C>CCO>[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]([NH:12][C:23]2[C:32]([C:33]#[N:34])=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[N:28][CH:29]=3)[N:24]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 110118554-Amino-N-((1,1-dimethylethoxy)carbonyl)-L-phenylalanine methyl esterHCID 12583775HCID 12583775, compound

Product 1

HCID 69375554(S)-2-tert-Butoxycarbonylamino-3-[4-(3-cyano[1,6]naphthyridin-2-ylamino)phenyl]propionic acid methyl esterYield 34.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (S)-3-(4-Aminophenyl)-2-tert-butoxycarbonylaminopropionic acid methyl ester (0.25 g, 0.84 mmol), 2-chloro[1,6]naphthyridine-3-carbonitrile (0.15 g, 0.77 mmol) (prepared according to the method of E. M. Hawes et al., J. Med. Chem. 1973,16, 849) and diisopropylethylamine (0.11 g, 0.84 mmol) in EtOH (1 ml) were heated under reflux for 3 h. The solvent was removed under reduced pressure and the resulting crude was purified by flash chromatography (CH2Cl2;AcOEt, 1:1) to yield (S)-2-tert-Butoxycarbonylamino-3-[4-(3-cyano[1,6]naphthyridin-2-ylamino)phenyl]propionic acid methyl ester (0.12 g, 34%) as a yellow solid.

Workup

  1. temperatureunder reflux for 3 h
  2. customThe solvent was removed under reduced pressure
  3. customthe resulting crude was purified by flash chromatography (CH2Cl2;AcOEt, 1:1)

Sources & evidence

ORD record
ord-5e4dce621c0e40ad89bb1dc1e3697d2b
Source dataset
uspto-grants-2007_08
Patent number
US07253171B2

Reaction notes

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