tert-Butylsulfinamide, (S)-(-)- → Benzyl 5-{[(S)-tert-butylsulfinyl]imino}-2,2-dimethylpentanoate

HRID 1866615Notes

Reaction equation

HRID 1866615 reaction equation
[CH3:1][C:2]([CH3:17])([CH2:13][CH2:14][CH:15]=O)[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[CH3:18][C:19]([S@@:22]([NH2:24])=[O:23])([CH3:21])[CH3:20]>C(Cl)Cl.[O-]S([O-])(=O)=O.[Cu+2]>[C:19]([S@@:22]([N:24]=[CH:15][CH2:14][CH2:13][C:2]([CH3:17])([CH3:1])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4])=[O:23])([CH3:21])([CH3:20])[CH3:18]

Participants

5

Reactant 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 86616388Benzyl 2,2-dimethyl-5-oxopentanoate

Product 1

HCID 66973494Benzyl 5-{[(S)-tert-butylsulfinyl]imino}-2,2-dimethylpentanoate

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of benzyl 2,2-dimethyl-5-oxopentanoate (1.06 g, 4.54 mmol, Step C) and anhydrous CuSO4 (1.59 g, 9.98 mmol) in DCM (10 mL) was added (S)-2-methylpropane-2-sulfinamide (0.550 g, 4.54 mmol). This mixture was stirred for 22 hours, before being filtered through a pad of celite. Additional DCM was used to wash the celite. The combined organics were concentrated in vacuo to give a residue that was purified by silica gel chromatography, eluting with a gradient of MeOH:DCM—0.5:99.5 to 1.5:98.5, to give the title compound. MS: m/z=338 (M+1).

Workup

  1. filtrationbefore being filtered through a pad of celite
  2. washto wash the celite
  3. concentrationThe combined organics were concentrated in vacuo
  4. customto give a residue that
  5. customwas purified by silica gel chromatography
  6. washeluting with a gradient of MeOH

Sources & evidence

ORD record
ord-32229c10a47044938d7ea25839e9d09a
Source dataset
uspto-grants-2009_12
Patent number
US07629338B2

Reaction notes

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