Propyl Isothiocyanate → HCID 178456539, compound

HRID 1882869Notes

Reaction equation

HRID 1882869 reaction equation
[CH2:1]([N:4]=[C:5]=[S:6])[CH2:2][CH3:3].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][NH:17][C@H:18]([C:30]2[NH:31][CH:32]=[C:33]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:34]=2)[CH2:19][C:20]([O:22]CC2C=CC=CC=2)=O)=[CH:8]1>C1COCC1>[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][N:17]2[C@H:18]([C:30]3[NH:31][CH:32]=[C:33]([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[N:34]=3)[CH2:19][C:20](=[O:22])[N:4]([CH2:1][CH2:2][CH3:3])[C:5]2=[S:6])=[CH:8]1

Participants

4

Reactant 2

HCID 69403Propyl IsothiocyanateHCID 178520773HCID 178520773, compound

Product 1

HCID 178456539HCID 178456539, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

Propylisothiocyanate (25 μl, 1.2 eq.) is added to a solution of benzyl (3S)-3-[(1H-indol-3-ylmethyl)amino]-3-(4-phenyl-1H-imidazol-2-yl)propanoate (90 mg, 1 eq.) in 2 ml of THF. The mixture is stirred for 15 hours at a temperature of approximately 40° C. then diluted with 2 ml of THF. An aminomethylpolystyrene resin (acquired from Novabiochem, load 3.2 mmol/g, 125 mg, 2 eq.) is added. The mixture is stirred for 5 hours at a temperature of approximately 20° C. then filtered on frit. The filtrate is concentrated under reduced pressure at 40° C. 1 ml of THF and 1 ml of triethylamine are added to the residue. The mixture is stirred for 15 hours at a temperature of approximately 40° C. then concentrated under reduced pressure. Purification by flash chromatography on silica gel (eluent: ethyl acetate/heptane 8:2) yields the expected compound (72 mg, yield 82%).

Workup

  1. additionAn aminomethylpolystyrene resin (acquired from Novabiochem, load 3.2 mmol/g, 125 mg, 2 eq.) is added
  2. stirringThe mixture is stirred for 5 hours at a temperature of approximately 20° C.
  3. filtrationthen filtered on frit
  4. concentrationThe filtrate is concentrated under reduced pressure at 40° C
  5. addition1 ml of THF and 1 ml of triethylamine are added to the residue
  6. stirringThe mixture is stirred for 15 hours at a temperature of approximately 40° C.
  7. concentrationthen concentrated under reduced pressure
  8. customPurification by flash chromatography on silica gel (eluent: ethyl acetate/heptane 8:2)

Sources & evidence

ORD record
ord-a6b486e5305f47f689b8675bfa4ecbdd
Source dataset
uspto-grants-2004_07
Patent number
US06759415B1

Reaction notes

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