Pyridine → HCID 54329957, compound

HRID 1872793Notes

Reaction equation

HRID 1872793 reaction equation
[OH:1][C@H:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:3][C:4]([NH2:6])=[O:5].N1C=CC=CC=1.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[CH3:26][S:27]([O:1][C@H:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:3][C:4]([NH2:6])=[O:5])(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 54536666HCID 54536666, compound

Product 1

HCID 54329957HCID 54329957, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-3-hydroxyhexadecanamide (100 mg) and pyridine (210 μl) in dichloromethane (10 ml) was added methanesulfonyl chloride (144 μl). This mixture was stirred at room temperature overnight, and the resulting precipitate was filtered off. The filtrate was concentrated, and dissolved in ethyl acetate (20 ml). This solution was washed with 1N-hydrochloric acid (20 ml×3), saturated sodium carbonate (20 ml×2), and brine (20 ml). After drying over MgSO4 and concentration, the residue was chromatographed on a silica gel, eluting with a mixture of dichloromethane and methanol (50:1) to give (R)-3-methanesulfonyloxyhexadecanamide (40 mg).

Workup

  1. filtrationthe resulting precipitate was filtered off
  2. concentrationThe filtrate was concentrated
  3. dissolutiondissolved in ethyl acetate (20 ml)
  4. washThis solution was washed with 1N-hydrochloric acid (20 ml×3), saturated sodium carbonate (20 ml×2), and brine (20 ml)
  5. dry with materialAfter drying over MgSO4 and concentration
  6. customthe residue was chromatographed on a silica gel
  7. washeluting with a mixture of dichloromethane and methanol (50:1)

Sources & evidence

ORD record
ord-bafbbbbf39364f8facf97e15d3307384
Source dataset
uspto-grants-2000_08
Patent number
US06110933

Reaction notes

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