Triethylamine → HCID 23533276, compound

HRID 2414240Notes

Reaction equation

HRID 2414240 reaction equation
C(N(CC)CC)C.[CH2:8]([N:22]([CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:64])[C:23]([CH2:25][CH2:26][C:27]([NH:29][CH2:30][CH2:31][NH:32][C:33](=[S:50])[NH:34][CH2:35][CH2:36][NH:37][C:38](=[S:49])[NH:39][CH2:40][CH2:41][NH:42][C:43](=[S:48])[NH:44][CH2:45][CH2:46][NH2:47])=[O:28])=[O:24])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[CH3:65][N:66]=[C:67]=[S:68]>C(Cl)Cl>[CH2:51]([N:22]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:23]([CH2:25][CH2:26][C:27]([NH:29][CH2:30][CH2:31][NH:32][C:33](=[S:50])[NH:34][CH2:35][CH2:36][NH:37][C:38](=[S:49])[NH:39][CH2:40][CH2:41][NH:42][C:43](=[S:48])[NH:44][CH2:45][CH2:46][NH:47][C:67](=[S:68])[NH:66][CH3:65])=[O:28])=[O:24])[CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:64]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11167Methyl isothiocyanateHCID 88050290HCID 88050290, compound

Product 1

HCID 23533276HCID 23533276, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.38 mmol, 0.19 ml) was directly added to the amine (14) (0.23 mmol, 0.224 g) obtained in the preceding stage and the reaction mixture was kept under stirring for 15 minutes. Then, CH2Cl2 (2.3 ml) and methylisothiocyanate (0.46 mmol, 0.034 g) were added and the reaction mixture was left at room temperature under stirring for 12 hours. The mixture was then evaporated and purified by flash chromatography (100% ethyl acetate followed by ethyl acetate/methanol 95:5). 109 mg of DT-4TU were thus obtained (yield: 51%).

Workup

  1. customobtained in the preceding stage
  2. waitthe reaction mixture was left at room temperature
  3. stirringunder stirring for 12 hours
  4. customThe mixture was then evaporated
  5. custompurified by flash chromatography (100% ethyl acetate followed by ethyl acetate/methanol 95:5)
  6. custom109 mg of DT-4TU were thus obtained (yield: 51%)

Sources & evidence

ORD record
ord-eee160ac7c4b4b089743f69f4ce3c410
Source dataset
uspto-grants-2004_11
Patent number
US06812218B2

Reaction notes

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