Dimethylformamide → HCID 86601512, compound

HRID 2222066Notes

Reaction equation

HRID 2222066 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[CH3:10][S:11](=[S:14])([O-:13])=[O:12].[Na+].[CH3:16]N(C)C=O>>[CH3:10][S:11](=[S:14])([O:13][CH2:16][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])=[O:12]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 202106-Bromohexanoic acidHCID 23688755Methanesulfonothioic acid, sodium salt

Product 1

HCID 86601512HCID 86601512, compoundYield 78%

Conditions

Temperature
55 °C

Procedure

6-Bromohexanoic acid (1.0 g, 5.1 mmol) and Sodium Methanethiosulfonate (750 mg, 5.6 mmol, 1.1 eq prepared according to Kenyon and Bruice, Methods Enzymol. (1977), 47, 407-430) were dissolved in 10 mL of dimethylformamide (DMF), warmed to 55° C. and stirred overnight. The reaction mixture was concentrated to syrup and taken up in CHCl3 (30 mL), washed with H2O (5×50 mL) and the organic phase was dried with anhydrous sodium sulfate. Concentration by rotary evaporation and elimination of residual solvent with high vacuum yielded 890 mg (78%) of white solid comprising 6-carboxyhexyl methanethiosulfonate. 1H NMR: δ 3.31 (s, 3H, CH3SO2S), 3.16 (t, J=7.5 Hz, 2H, SCH2), 2.37 (t, J=7.2 Hz, 2H, CH2COOH), 1.79 (m, 2H, CH2CH2S), 1.67 (m, 2H, CH2CH2COOH), 1.48 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated to syrup
  2. washwashed with H2O (5×50 mL)
  3. dry with materialthe organic phase was dried with anhydrous sodium sulfate
  4. concentrationConcentration
  5. customby rotary evaporation and elimination of residual solvent with high vacuum

Sources & evidence

ORD record
ord-fe8bb200e434406db6b8e3112d2e024a
Source dataset
uspto-grants-2008_05
Patent number
US07371585B2

Reaction notes

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