Ethanol → (2-(Benzyloxycarbonylamino)-2-methylpropyl)dimethylsulfonium iodide

HRID 2061057Notes

Reaction equation

HRID 2061057 reaction equation
[CH3:1][C:2]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:6])[CH2:3][S:4][CH3:5].[CH2:18](O)C.C[I:22].[Al]>>[I-:22].[CH2:10]([O:9][C:8]([NH:7][C:2]([CH3:1])([CH3:6])[CH2:3][S+:4]([CH3:18])[CH3:5])=[O:17])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 6328Methyl iodideHCID 5359268AluminumHCID 60134425Benzyl 1,1-dimethyl-2-(methylthio)ethylcarbamate

Product 1

HCID 86642699(2-(Benzyloxycarbonylamino)-2-methylpropyl)dimethylsulfonium iodide

Procedure

To a 15 mL pressure tube was added a solution of benzyl 2-methyl-1-(methylthio)propan-2-ylcarbamate in absolute ethanol (0.5 mL, 6.8 M) (1.00 g, 3.9 mmol) and methyl iodide (1.23 mL, 5 equiv, 19.7 mmol). The reaction mixture was covered with aluminum foil and left to stir for 3 days. The light yellow suspension was filtered and washed with diethyl ether (20 mL). The mother liquor was concentrated to a deep yellow solid. This solid was recrystallized from isopropyl alcohol and diethyl ether and combined with the first crop of product 1.29 g (83.6%). 1H NMR (D2O, 400 MHz): δ 1.41 (s, 6H), 2.51 (s, 2H), 2.98 (s, 2 H). LRMS (ESI−) for C14H22NO2S+ (268.1); Found: 268 (M+).

Workup

  1. waitleft
  2. filtrationThe light yellow suspension was filtered
  3. washwashed with diethyl ether (20 mL)
  4. concentrationThe mother liquor was concentrated to a deep yellow solid
  5. customThis solid was recrystallized from isopropyl alcohol and diethyl ether

Sources & evidence

ORD record
ord-730c2a2825f1404db23fe86e5eaf3291
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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