Trifluoromethanesulfonic acid, lithium salt → (R)-[3-(1-ethyl-7-fluoro-2-oxo-2,3-dihydro-1H-indol-5-ylamino)-2-hydroxy-propyl]-carbamic acid tert-butyl ester

HRID 2114881Notes

Reaction equation

HRID 2114881 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][CH3:13])[C:6](=[O:14])[CH2:5]2.[C:15]([O:19][C:20](=[O:26])[NH:21][CH2:22][C@H:23]1[CH2:25][O:24]1)([CH3:18])([CH3:17])[CH3:16].FC(F)(F)S([O-])(=O)=O.[Li+]>C(#N)C.C(OCC)(=O)C>[C:15]([O:19][C:20](=[O:26])[NH:21][CH2:22][C@H:23]([OH:24])[CH2:25][NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[N:7]([CH2:12][CH3:13])[C:6](=[O:14])[CH2:5]2)([CH3:17])([CH3:16])[CH3:18]

Participants

6

Reactant 3

HCID 3664839Trifluoromethanesulfonic acid, lithium saltHCID 10080852(S)-N-Boc-2,3-epoxypropylamineHCID 692727925-Amino-1-ethyl-7-fluoro-1,3-dihydro-indol-2-one

Product 1

HCID 69274203(R)-[3-(1-ethyl-7-fluoro-2-oxo-2,3-dihydro-1H-indol-5-ylamino)-2-hydroxy-propyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Amino-1-ethyl-7-fluoro-1,3-dihydro-indol-2-one (2.25 g, 11.6 mmol), (S)-oxiranylmethyl-carbamic acid tert-butyl ester (2.00 g, 11.6 mmol) and lithium trifluoromethanesulfonate (1.80 g, 11.6 mmol) in acetonitrile (12 ml) are heated at 90° C. for 20 hours. The reaction mixture is diluted with ethyl acetate, washed with water and brine, dried (Na2SO4) and evaporated. Final purification by flash chromatography (70% Ethyl acetate/hexane) gives the title compound as a yellow-brown foamy solid. HPLC r.t. 3.95 min; MS for C 18H26FN3O4 m/z 368.3 (M+H)+.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customFinal purification by flash chromatography (70% Ethyl acetate/hexane)

Sources & evidence

ORD record
ord-62a438a2d93c4d80aba6aa6a14229963
Source dataset
uspto-grants-2008_10
Patent number
US07435751B2

Reaction notes

Loading…