Triethylamine → HCID 23509796, compound

HRID 1268967Notes

Reaction equation

[N+]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]=[S:12])=[CH:6][CH:5]=1)([O-])=O.[NH:13]1[C:21]2C(=CC=CC=2)C(CN[C@@H](CCC2NC=C(C3C=CC=CC=3)N=2)C(OCC2C=CC=CC=2)=O)=[CH:14]1.C(N(CC)CC)C>C1COCC1>[N:10]([CH2:7][CH2:8][CH2:9][CH2:4][CH2:5][CH2:6][N:13]([CH3:21])[CH3:14])=[C:11]=[S:12]

Participants

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

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

Sources & evidence

ORD record: ord-f6a0e9c9e814458fb1fb656b94f49539
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199145B2

Reaction notes

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