Diethyl Ether → Methyl (5S)-5-[(tert-butylsulfinyl)amino]-5-(3,5-difluorophenyl)-2,2-dimethylhexanoate

HRID 1864921Notes

Reaction equation

HRID 1864921 reaction equation
[C:1]([S:5](/[N:7]=[C:8](/[C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=1)\[CH2:9][CH2:10][C:11]([CH3:17])([CH3:16])[C:12]([O:14][CH3:15])=[O:13])=[O:6])([CH3:4])([CH3:3])[CH3:2].[CH3:26][Mg]Br.C(OCC)C>C(Cl)Cl>[C:1]([S:5]([NH:7][C@@:8]([C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=1)([CH3:26])[CH2:9][CH2:10][C:11]([CH3:16])([CH3:17])[C:12]([O:14][CH3:15])=[O:13])=[O:6])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 87221342methyl (5E)-5-tert-butylsulfinylimino-5-(3,5-difluorophenyl)-2,2-dimethylpentanoateHCID 178418573HCID 178418573, compound

Product 1

HCID 66973479Methyl (5S)-5-[(tert-butylsulfinyl)amino]-5-(3,5-difluorophenyl)-2,2-dimethylhexanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl (5E)-5-[(tert-butylsulfinyl)imino]-5-(3,5-difluorophenyl)-2,2-dimethylpentanoate (342 mg, 0.920 mmol) in CH2Cl2 (6 mL) at 0° C., was added dropwise over five minutes methyl magnesium bromide as a 3M solution in diethyl ether (0.61 mL, 1.83 mmol). After 15 minutes the reaction was determined to be complete by LCMS analysis. The reaction was quenched by the dropwise addition of 1M HCl (5 mL), followed by 5 mL of water. The aqueous layer was extracted once with CH2Cl2 (10 mL) and the organics were combined and washed once with brine (15 mL). The organics were dried over sodium sulfate, filtered and concentrated in vacuo to give a residue that was purified by silica gel chromatography, eluting with a gradient of EtOAc:Hexanes-10:90 to 55:45, to give the title compound. MS: m/z=390 (M+1).

Workup

  1. customThe reaction was quenched by the dropwise addition of 1M HCl (5 mL)
  2. extractionThe aqueous layer was extracted once with CH2Cl2 (10 mL)
  3. washwashed once with brine (15 mL)
  4. dry with materialThe organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a residue that
  8. customwas purified by silica gel chromatography
  9. washeluting with a gradient of EtOAc

Sources & evidence

ORD record
ord-f408b55853614a9793115030d0b7acc4
Source dataset
uspto-grants-2009_12
Patent number
US07625901B2

Reaction notes

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