Acetyl chloride → [2-Methanesulfonyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-carbamic acid benzyl ester

HRID 1480172Notes

Reaction equation

HRID 1480172 reaction equation
[CH2:1]([O:8][C:9](=[O:22])[NH:10][C:11]([C:18](=[NH:21])[NH:19][OH:20])([CH3:17])[CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23](N(CC)CC)[CH3:24].C(Cl)(=O)C>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:22])[NH:10][C:11]([CH3:17])([C:18]1[N:21]=[C:23]([CH3:24])[O:20][N:19]=1)[CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178460881HCID 178460881, compound

Product 1

HCID 90203952[2-Methanesulfonyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-carbamic acid benzyl esterYield 55.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of [1-(N-Hydroxycarbamimidoyl)-2-methanesulfonyl-1-methyl-ethyl]-carbamic acid benzyl ester (Example 109b, 2.04 g, 6.19 mmol) in dry DMF (30 mL) were added triethylamine (1.73 mL, 12.4 mmol) and acetyl chloride (572 μL, 8.05 mmol). the reaction was stirred 30 minutes at room temperature. Reaction was then stirred at 130° C. for 18 hours. The reaction mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate and extracted with an 1.0M aqueous solution of sodium bicarbonate. The organic layer was dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient to yield the title compound (1.21 g, 55%) as yellow oil. MS (ESI, m/z): 354.5 (M+H+).

Workup

  1. customReaction
  2. stirringwas then stirred at 130° C. for 18 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. extractionextracted with an 1.0M aqueous solution of sodium bicarbonate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customevaporated down to dryness
  8. customThe crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient

Sources & evidence

ORD record
ord-a03fc7514c9b4c5da0e4e7586e7b37bf
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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