Trifluoroacetic acid → (S)-2-Amino-3-[4-([2,6]naphthyridin-1-ylamino)phenyl] propionic acid methyl ester

HRID 852252Notes

Reaction equation

HRID 852252 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C@@H:4]([NH:23]C(OC(C)(C)C)=O)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[C:22]3[C:17](=[CH:18][N:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][N:14]=2)=[CH:8][CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3](=[O:31])[C@@H:4]([NH2:23])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13]2[C:22]3[C:17](=[CH:18][N:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][N:14]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69376816HCID 69376816, compound

Product 1

HCID 69376840(S)-2-Amino-3-[4-([2,6]naphthyridin-1-ylamino)phenyl] propionic acid methyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-2-tert-butoxycarbonylamino-3-[4-([2,6]naphthyridin-1-ylamino)phenyl] propionic acid methyl ester (405 mg, 0.96 mmol) in dichloromethane (11.5 ml) was, treated with trifluoroacetic acid (11.5 ml) and stirred at room temperature for 2 h. The volatiles were removed in vacuo and the residue was partitioned between EtOAc (80 ml) and saturated aqueous NaHCO3 (30 ml). The phases were separated and the aqueous layer re-extracted with EtOAc (3×30 ml). The combined organic extracts were dried (MgSO4) and evaporated in vacuo to afford the title compound (308 mg, 100%) as a dark viscous oil.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue was partitioned between EtOAc (80 ml) and saturated aqueous NaHCO3 (30 ml)
  3. customThe phases were separated
  4. extractionthe aqueous layer re-extracted with EtOAc (3×30 ml)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-b9f90fb5bdf24ecbb691789d0b27da4a
Source dataset
uspto-grants-2007_08
Patent number
US07253171B2

Reaction notes

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