Triethylamine → HCID 131711389, compound

HRID 2163177Notes

Reaction equation

HRID 2163177 reaction equation
[NH:1]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C@H:2]([C:6]([N:8]1[CH2:28][CH2:27][CH2:26][C@H:9]1[C:10]([NH:12][CH2:13][C:14](OC1C=CC([N+]([O-])=O)=CC=1)=[O:15])=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4].[NH2:36][C@H:37]([C:48]([NH:50][CH2:51][C:52]([O:54][CH3:55])=[O:53])=[O:49])[CH2:38][CH:39]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[C:40](=[O:42])[OH:41].Cl.C(N(CC)CC)C>CN(C)C=O>[NH:1]([C:29]([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30])[C@H:2]([C:6]([N:8]1[CH2:28][CH2:27][CH2:26][C@H:9]1[C:10]([NH:12][CH2:13][C:14]([NH:36][C@H:37]([C:48]([NH:50][CH2:51][C:52]([O:54][CH3:55])=[O:53])=[O:49])[CH2:38][CH:39]([O:43][C:44]([CH3:45])([CH3:46])[CH3:47])[C:40](=[O:41])[OH:42])=[O:15])=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 131711387HCID 131711387, compoundHCID 131711390HCID 131711390, compound

Product 1

HCID 131711389HCID 131711389, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of XV (1.66 g, 3.38 mmol) in dimethyl formamide (5 ml) were added XVII (1.05 g, 3.38 mmol) and triethylamine (0.57 ml, 4.06 mmol) in dimethyl formamide (5 ml) and the mixture was stirred for 2 days at room temperature. The reaction mixture was evaporated and the residue, dissolved in ethyl acetate, was washed with 10% citric acid solution, 4% sodium bicarbonate solution, water and dried over sodium sulfate. The solution was evaporated to dryness. An oil obtained gave a single spot on TLC; yield 1.64 g (77%), Rf1 0.57.

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe residue, dissolved in ethyl acetate
  3. washwas washed with 10% citric acid solution, 4% sodium bicarbonate solution, water
  4. dry with materialdried over sodium sulfate
  5. customThe solution was evaporated to dryness
  6. customAn oil obtained
  7. customgave a single spot on TLC

Sources & evidence

ORD record
ord-cd47011e6b174f599f03b7ebb2039725
Source dataset
uspto-grants-1979_01
Patent number
US04132746

Reaction notes

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