L-Lysine → 5-(4-Benzyloxycarbonylaminobutyl)-3-methyl-2-thiohydantoin

HRID 1287290

Reaction equation

HRID 1287290 reaction equation
CO[C:3](=[O:21])[C@H:4]([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[NH2:5].N[C@H](C(O)=O)CCCCN.[CH3:32][N:33]=[C:34]=[S:35]>C(#N)C>[CH2:14]([O:13][C:11]([NH:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:4]1[NH:5][C:34](=[S:35])[N:33]([CH3:32])[C:3]1=[O:21])=[O:12])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 5962L-LysineHCID 11167Methyl isothiocyanateHCID 6994982methyl (2S)-2-amino-6-(phenylmethoxycarbonylamino)hexanoate

Product 1

HCID 215076825-(4-Benzyloxycarbonylaminobutyl)-3-methyl-2-thiohydantoinYield 22.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of Nε-benzyloxycarbonyl-L-lysine methyl ester (4.66 g., 0.016 mol.) (prepared from L-lysine according to the method of Bergmann et al., J. Biol. Chem. 1935, 111, 245) in acetonitrile (20 ml.) was treated with methyl isothiocyanate (1.16 g., 0.016 mol.) and the mixture heated at reflux for 3 hours. The solvent was removed in vacuo and the residual oil triturated with ethanol to give a white solid which recrystallised from ethanol to give the title compound as colourless needles (1.2 g.) m.p. 135°C. (Found: C, 57.3; H, 6.4; N, 12.2; C16H21N3O3S requires: C, 57.3; H, 6.3; N, 12.5%).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 3 hours
  3. customThe solvent was removed in vacuo
  4. customthe residual oil triturated with ethanol
  5. customto give a white solid which
  6. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-ac5d9645333b464685fd8da40dd721f4
Source dataset
uspto-grants-1976_10
Patent number
US03984430

Linked notes

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