Trifluoromethanesulfonic acid, lithium salt → (R)-3-(7-Fluoro-2-oxo-1-propyl-2,3-dihydro-1H-indol-5-ylamino)-2-hydroxy-propionic acid methyl ester

HRID 2114893Notes

Reaction equation

HRID 2114893 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[N:7]([CH2:12][CH2:13][CH3:14])[C:6](=[O:15])[CH2:5]2.[CH3:16][O:17][C:18]([C@@H:20]1[O:22][CH2:21]1)=[O:19].FC(F)(F)S([O-])(=O)=O.[Li+]>C(#N)C.C(OCC)(=O)C>[CH3:16][O:17][C:18](=[O:19])[C@H:20]([OH:22])[CH2:21][NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[N:7]([CH2:12][CH2:13][CH3:14])[C:6](=[O:15])[CH2:5]2

Participants

6

Reactant 3

HCID 3664839Trifluoromethanesulfonic acid, lithium saltHCID 9877347Methyl (2R)-2-oxiranecarboxylateHCID 692741315-Amino-7-fluoro-1-propyl-1,3-dihydro-indol-2-one

Product 1

HCID 69274128(R)-3-(7-Fluoro-2-oxo-1-propyl-2,3-dihydro-1H-indol-5-ylamino)-2-hydroxy-propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Amino-7-fluoro-1-propyl-1,3-dihydro-indol-2-one (0.300 g, 1.44 mmol), methyl (2R)-glycidate (0.147 g, 1.44 mmol) and lithium trifluoromethanesulfonate (0.220 g, 1.44 mmol) in acetonitrile (5 ml) are heated at 90° C. for 8 hours. The reaction is diluted with ethyl acetate, washed with water and brine, dried (Na2SO4) and evaporated. The residue is purified by PTLC (5% methanol/dichloromethane) to give the title compound as a yellow solid. HPLC r.t. 4.03 min; MS for C15H19FN2O4 m/z 311.2 (M+H)+.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe residue is purified by PTLC (5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-9a2ed9b7546049059c0e7b844a3ceec7
Source dataset
uspto-grants-2008_10
Patent number
US07435751B2

Reaction notes

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