Triethylamine → methyl N-acetyl-3-[(1-propylbutyl)sulfonyl]alaninate

HRID 857264Notes

Reaction equation

HRID 857264 reaction equation
[C:1]([NH:4][C:5](=[CH2:10])[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2].S[CH:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15].C(N(CC)CC)C.O[O:27][S:28]([O-:30])=O.[K+]>CO>[C:1]([NH:4][C@H:5]([C:6]([O:8][CH3:9])=[O:7])[CH2:10][S:28]([CH:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])(=[O:30])=[O:27])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 98644Methyl 2-acetamidoacrylateHCID 12627260HCID 12627260, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 86589164methyl N-acetyl-3-[(1-propylbutyl)sulfonyl]alaninate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-acetamidoacrylate (LXXX, 5.0 g, 34 mmole) and 4-mercaptoheptane (4.6 g, 34 mmole) in methanol (50 ml) are mixed. Triethylamine (3.6 g, 36 mmole) is added and the mixture is stirred at 20–25° for 45 minutes. The reaction vessel is then treated with oxone (47.2 g, 77 mmole). After 90 minutes HPLC indicated complete oxidation to the desired sulfone (LXXXII). The reaction mixture is filtered and concentrated under reduced pressure. The residue is partitioned between ethyl acetate and water and the organic phase is separate and is washed with saline, dried over sodium sulfate, and concentrated under reduced pressure to give methyl N-acetyl-3-[(1-propylbutyl)sulfonyl]alaninate (LXXXII), M+H=308 g/m.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is partitioned between ethyl acetate and water
  4. customthe organic phase is separate
  5. washis washed with saline
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-12cfae7b8cdf4594b9dbba2ee25d5af4
Source dataset
uspto-grants-2006_12
Patent number
US07144897B2

Reaction notes

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