Triethylamine → HCID 178516688, compound

HRID 1882867Notes

Reaction equation

HRID 1882867 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]=[S:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][NH:23][C@@H:24]([CH2:35][CH2:36][C:37]2[NH:38][CH:39]=[C:40]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[N:41]=2)[C:25](OCC2C=CC=CC=2)=[O:26])=[CH:14]1.C(N(CC)CC)C>C1COCC1>[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][N:23]2[C@@H:24]([CH2:35][CH2:36][C:37]3[NH:38][CH:39]=[C:40]([C:42]4[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=4)[N:41]=3)[C:25](=[O:26])[N:10]([C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=3)[C:11]2=[S:12])=[CH:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75044Benzene, 1-isothiocyanato-4-nitro-HCID 178525089HCID 178525089, compound

Product 1

HCID 178516688HCID 178516688, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

4-nitro-phenylisothiocyanate (43 mg; 1.2 eq.) is added to a solution of benzyl (2S)-2-[(1H-indol-3-ylmethyl)amino]-4-(4-phenyl-1H-imidazol-2-yl)butanoate (93 mg; 1 eq.) in THF (2 ml). The mixture is stirred for 2 hours at approximately 20° C. then diluted with 4 ml of THF. Aminomethylpolystyrene resin (acquired from Novabiochem, load 3.2 mmol/g, 125 mg, 2 eq.) is added, then triethylamine (200 μl). The mixture is stirred for 15 hours at approximately 20° C. then filtered on frit. The filtrate is concentrated to dryness under reduced pressure at 40° C. (a co-evaporation with dichloromethane is necessary to eliminate the excess triethylamine). Purification of the residue by flash chromatography on silica gel (eluent: ethyl acetate/heptane 9:1) yields the expected compound (90 mg; 84% yield).

Workup

  1. additionAminomethylpolystyrene resin (acquired from Novabiochem, load 3.2 mmol/g, 125 mg, 2 eq.) is added
  2. stirringThe mixture is stirred for 15 hours at approximately 20° C.
  3. filtrationthen filtered on frit
  4. concentrationThe filtrate is concentrated to dryness under reduced pressure at 40° C. (a co-evaporation with dichloromethane
  5. customPurification of the residue by flash chromatography on silica gel (eluent: ethyl acetate/heptane 9:1)

Sources & evidence

ORD record
ord-d5ab38e252c4462ba22191f2ef7f6a80
Source dataset
uspto-grants-2004_07
Patent number
US06759415B1

Reaction notes

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