Trifluoroacetic acid → HCID 69378472, compound

HRID 852253Notes

Reaction equation

HRID 852253 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]([O: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]([O: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 53746769HCID 53746769, compound

Product 1

HCID 69378472HCID 69378472, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-2-tert-butoxycarbonylamino-3-[4-([2,6]naphthyridin-1-yloxy)phenyl]propionic acid methyl ester (271 mg, 0.64 mmol) in dichloromethane (7.5 ml) was treated with trifluoroacetic acid (7.5 ml) and stirred at room temperature for 2 h. The volatiles were removed in vacuo and the residue was partitioned between EtOAc (60 ml) and saturated aqueous NaHCO3 (25 ml). The phases were separated and the aqueous layer re-extracted with EtOAc (3×25 ml). The combined organic extracts were dried (MgSO4) and evaporated in vacuo to afford the title compound (206 mg, 100%) as an oil that was used in the next step without further purification.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue was partitioned between EtOAc (60 ml) and saturated aqueous NaHCO3 (25 ml)
  3. customThe phases were separated
  4. extractionthe aqueous layer re-extracted with EtOAc (3×25 ml)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-b4ae19f0fa2c499d9bf0beb0ab5289ea
Source dataset
uspto-grants-2007_08
Patent number
US07253171B2

Reaction notes

Loading…