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Ethyl Acetate → N-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-6-methylphenyl)-1-(2,3-dihydroxypropyl)cyclopropane-1-sulfonamide

HRID 240974
Notes
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Reaction equation

HRID 240974 reaction equation
[CH2:1]([C:4]1([S:7]([NH:10][C:11]2[C:16]([CH3:17])=[CH:15][C:14]([F:18])=[C:13]([F:19])[C:12]=2[NH:20][C:21]2[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=2[F:28])(=[O:9])=[O:8])[CH2:6][CH2:5]1)C=C.C[N+]1([O-])CC[O:33]CC1.CCO[C:40]([CH3:42])=[O:41]>C1COCC1.O.[Os](=O)(=O)(=O)=O>[F:19][C:13]1[C:12]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=2[F:28])=[C:11]([NH:10][S:7]([C:4]2([CH2:1][CH:40]([OH:41])[CH2:42][OH:33])[CH2:6][CH2:5]2)(=[O:9])=[O:8])[C:16]([CH3:17])=[CH:15][C:14]=1[F:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 82029Methyl morpholine oxideHCID 593863781-Allyl-N-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-6-methylphenyl)cyclopropane-1-sulfonamide

Product 1

HCID 53492359N-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-6-methylphenyl)-1-(2,3-dihydroxypropyl)cyclopropane-1-sulfonamideYield 68%

Reagents, catalysts & solvents 3

HCID 30318
Osmium Tetroxide
Catalyst
HCID 962WaterSolvent
HCID 8028TetrahydrofuranSolvent

Procedure

1-Allyl-N-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-6-methylphenyl)cyclopropane-1-sulfonamide (150 mg, 0.29 mmol) and 4-methylmorpholine N-oxide (33 mg, 0.29 mmol) was dissolved in THF (5 mL). Osmium tetroxide was added at room temperature (0.029 mmol, 0.18 mL, 4% in H2O) and the reaction mixture was stirred at room temperature for 16 hours. EtOAc was added, the organic phase was washed with water, dried (MgSO4) and concentrated under reduced pressure. The residue was purified over silica gel chromatography (eluants: EtOAc/MeOH) to obtain the titled product (0.110 g, 68%). 1H-NMR (300 MHz, CDCl3): δ 7.07 (m, 1H), 6.97 (br m, 2H), 6.84 (m, 2H), 6.60 (br m, 2H), 3.98 (br m, 1H), 3.58 (m, 1H), 3.43 (m, 1H), 3.20 (d, J=3.9 Hz, 1H), 2.42 (s, 3H), 2.31 (dd, J=9.9 & 15.6 Hz, 1H), 2.01 (br t, 1H), 2.31 (dd, J=9.9 & 15.6 Hz, 1H), 1.66 (dd, J=2.1 & 15.9 Hz, 1H), 1.52 (m, 1H), 1.40 (m, 1H), 0.91 (m, 2H).

Workup

  1. washthe organic phase was washed with water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified over silica gel chromatography (eluants: EtOAc/MeOH)

Sources & evidence

ORD record
ord-89f8857e7d174af9bc7e8c85cc8c245d
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08648116B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes