1,2-Dichloroethane → S-3-(4-(4-(4-(4-(tert-butoxycarbonylamino)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-imidazole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxamido)-N, 1-dimethyl-1H-pyrrole-2-carboxamido)propyl ethanethioate

HRID 1776677

Reaktionsgleichung

Reaktionsgleichung von HRID 1776677
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([C:15]([NH:17][C:18]2[N:19]=[C:20]([C:24]([NH:26][C:27]3[CH:28]=[C:29]([C:33]([NH:35][C:36]4[CH:37]=C(C(O)=O)[N:39]([CH3:41])[CH:40]=4)=[O:34])[N:30]([CH3:32])[CH:31]=3)=[O:25])[N:21]([CH3:23])[CH:22]=2)=[O:16])[N:12]([CH3:14])[CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.Cl.[C:50](=[O:58])([S:52][CH2:53][CH2:54]CNC)[CH3:51].[CH3:59][C:60]([N:62]([CH3:64])[CH3:63])=[O:61]>>[C:50](=[O:58])([S:52][CH2:53][CH2:54][CH2:63][N:62]([CH3:64])[C:60]([C:59]1[N:39]([CH3:41])[CH:40]=[C:36]([NH:35][C:33]([C:29]2[N:30]([CH3:32])[CH:31]=[C:27]([NH:26][C:24]([C:20]3[N:21]([CH3:23])[CH:22]=[C:18]([NH:17][C:15]([C:11]4[N:12]([CH3:14])[CH:13]=[C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:10]=4)=[O:16])[N:19]=3)=[O:25])[CH:28]=2)=[O:34])[CH:37]=1)=[O:61])[CH3:51]

Komponenten

5

Edukt 4

HCID 111,2-DichloroethaneHCID 31374DimethylacetamideHCID 594400974-(4-(4-(4-(tert-butoxycarbonylamino)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-imidazole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxylic acidHCID 86644083S-3-(Methylamino)propyl ethanethioate hydrogen chloride salt

Produkt 1

HCID 59440243S-3-(4-(4-(4-(4-(tert-butoxycarbonylamino)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-imidazole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxamido)-N, 1-dimethyl-1H-pyrrole-2-carboxamido)propyl ethanethioateAusbeute 64 %

Versuchsvorschrift

4-(4-(4-(4-(tert-butoxycarbonylamino)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1 H-imidazole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxylic acid (256 mg, 0.42 mmol), NHS (60 mg, 0.52 mmol) and EDC (500 mg, 2.60 mmol) in 4 ml of DMA were stirred under Ar for 2 h, then S-3-(methylamino)propyl ethanethioate hydrogen chloride salt (76.5 mg, 0.42 mmol) was added and the mixture was kept stirring for 24 h, evaporated and purified on SiO2 chromatography eluted with THF/DCM (1:5 to 1:4) to afford 198 mg (64%) of the title compound. 1H NMR (DMSO) 10.21 (s, 1H), 10.09 (s, 1H), 10.06 (s, 1H), 9.08 (s, 1H), 7.76 (d, 1H, J=1.7 Hz), 7.52 (s, 1H), 7.28 (s, 1H), 7.21 (d, 1H, J=1.7 Hz), 6.97 (s, 1H), 6.87 (s, 1H), 3.98 (s, 1H), 3.86 (s, 3H), 3.75 (s, 3H), 3.73 (s, 3H), 3.66 (m, 2H), 2.85 (s, 3H), 2.60 (m, 2H), 2.01 (s, 3H), 1.45 (s, 9H); 13C NMR 173.31, 162.16, 160.05, 159.90, 157.20, 154.31, 137.88, 135.35, 124.56, 124.39, 123.51, 123.09, 121.76, 120.09, 119.83, 118.96, 115.32, 109.53, 105.58, 102.27, 79.32, 43.67, 38.13, 36.02, 35.81, 34.88, 31.84, 28.79, 28.26, 28.21, 27.01; MS m/z+759.2 (M+Na).

Aufarbeitung

  1. customevaporated
  2. custompurified on SiO2 chromatography
  3. washeluted with THF/DCM (1:5 to 1:4)

Quellen und Nachweise

ORD-Eintrag
ord-3a519210f6664b29825d93d666158f45
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09265841B2

Verknüpfte Notizen

Wird geladen…