p-Toluenesulfonic acid → HCID 86608885, compound

HRID 1433314Notes

Reaction equation

HRID 1433314 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([OH:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH2:12][C@@:13]([CH3:23])([CH2:17][CH:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[C:14]([OH:16])=[O:15]>C(#N)C>[C:1]1([CH3:11])[CH:2]=[CH:3][C:4]([S:7]([OH:10])(=[O:8])=[O:9])=[CH:5][CH:6]=1.[NH2:12][C@@:13]([CH3:23])([CH2:17][CH:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 11845859HCID 11845859, compound

Product 1

HCID 86608885HCID 86608885, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of p-toluene sulphonic acid (54 mg, 0.28 mmol) in acetonitrile (1 ml) was added to a suspension of (2S)-2-Amino-4-ethyl-2-methylhexanoic acid (50 mg, 0.28 mmol, Example 1) in acetonitrile (1 ml) and the mixture heated until dissolved. The solution was filtered whilst hot and allowed to cool overnight to give the title compound as fine white needles, (69 mg, 70%)

Workup

  1. temperaturethe mixture heated
  2. dissolutionuntil dissolved
  3. filtrationThe solution was filtered whilst hot and
  4. temperatureto cool overnight

Sources & evidence

ORD record
ord-6d194cd94b614618852b2e7483a18ab2
Source dataset
uspto-grants-2009_11
Patent number
US07612226B2

Reaction notes

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