Trifluoroacetic acid → 3-(6-hydroxy-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-1-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3-dihydro-2H-indol-2-one trifluoroacetate

HRID 2385016Notes

Reaction equation

HRID 2385016 reaction equation
C([SiH](CC)CC)C.O[C:9]1([C:25]2[C:35]([OH:36])=[CH:34][C:28]3[N:29]([CH3:33])[CH2:30][CH2:31][O:32][C:27]=3[CH:26]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:18][C@H:19]2[CH2:23][CH2:22][CH2:21][O:20]2)[C:10]1=[O:24].[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40]>ClCCl>[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40].[OH:36][C:35]1[C:25]([CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:18][C@H:19]3[CH2:23][CH2:22][CH2:21][O:20]3)[C:10]2=[O:24])=[CH:26][C:27]2[O:32][CH2:31][CH2:30][N:29]([CH3:33])[C:28]=2[CH:34]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 685987153-hydroxy-3-(6-hydroxy-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-1-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3-dihydro-2H-indol-2-one

Product 1

HCID 685974793-(6-hydroxy-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-1-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3-dihydro-2H-indol-2-one trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of triethylsilane (1.3 mL, 8.2 mmol) in trifluoroacetic acid (8 mL) was added dropwise a solution of 3-hydroxy-3-(6-hydroxy-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-1-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3-dihydro-2H-indol-2-one (1.04 g, 2.62 mmol) in dichloromethane (3 mL). The resulting solution was warmed to reflux and stirred under nitrogen for 90 min. Once cooled, the solvent was removed under reduced pressure to afford 3-(6-hydroxy-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-1-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3-dihydro-2H-indol-2-one trifluoroacetate as a light brown foam: MS (ES+) m/z 381.0 (M+1).

Workup

  1. temperatureThe resulting solution was warmed
  2. temperatureto reflux
  3. temperatureOnce cooled
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3e97f6fc5842442ca55c20ffd1e565a6
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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