Triethylamine → N-tert-butyl-N'-[(1R,2S)-1-(4-pyridylmethyl)-2-hydroxybutyl]thiourea

HRID 47783Notes

Reaction equation

HRID 47783 reaction equation
C(N(CC)CC)C.Cl.Cl.[NH2:10][C@@H:11]([C@@H:19]([OH:22])[CH2:20][CH3:21])[CH2:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.[C:23]([N:27]=[C:28]=[S:29])([CH3:26])([CH3:25])[CH3:24]>C(O)C>[C:23]([NH:27][C:28]([NH:10][C@H:11]([CH2:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)[C@@H:19]([OH:22])[CH2:20][CH3:21])=[S:29])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11544tert-Butyl isothiocyanateHCID 69885274HCID 69885274, compound

Product 1

HCID 86584450N-tert-butyl-N'-[(1R,2S)-1-(4-pyridylmethyl)-2-hydroxybutyl]thiourea

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

4.3 cm3 of triethylamine are added to a solution of 3.6 g of (2R,3S)-2-amino-1-(4-pyridyl)-3-pentanol dihydrochloride in 60 cm3 of ethanol, followed by addition of 2.6 cm3 of tert-butyl isothiocyanate. The mixture is heated at a temperature in the region of 50° C. for 18 hours. After cooling, the reaction medium is concentrated under reduced pressure (1 kPa) at a temperature in the region of 40° C. and the residue is taken up in 50 cm3 of water and 100 cm3 of dichloromethane. The organic phase is washed with 30 cm3 of water, dried over sodium sulfate, filtered and concentrated under the above conditions. 4.3 g of N-tert-butyl-N′-[(1R,2S)-1-(4-pyridylmethyl)-2-hydroxybutyl]thiourea are obtained in the form of a thick colorless oil [1H NMR spectrum (300 MHz, (CD3)2SO-d6, δ in ppm): 0.80 (t, J=7.5 Hz: 3H); from 1.25 to 1.55 (mt: 2H); 1.37 (s: 9H); 2.72 (dd, J=14 and 9 Hz: 1H); 2.93 (dd, J=14 and 4.5 Hz: 1H); 3.37 (mt: 1H); 4.60 (mt: 1H); 4.88 (unresolved complex: 1H); 7.11 (s: 1H); 7.16 (d, J=8.5 Hz: 1H); 7.26 (broad d, J=5.5 Hz: 2H); 8.43 (broad d, J=5.5 Hz: 2H)].

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction medium is concentrated under reduced pressure (1 kPa) at a temperature in the region of 40° C.
  3. washThe organic phase is washed with 30 cm3 of water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under the above conditions

Sources & evidence

ORD record
ord-06d7895654df4fe88aca823c98f44997
Source dataset
uspto-grants-2004_03
Patent number
US06699895B2

Reaction notes

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