Triethylamine → HCID 57860149, compound

HRID 1947147Notes

Reaction equation

HRID 1947147 reaction equation
Cl.[CH3:2][O:3][C:4]1[C:8]2[C:9](=[O:26])[N:10]([CH2:17][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[C:7]=2[N:6]([CH3:27])[C:5]=1[C:28]([NH:30][CH2:31][CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)=[O:29].C(N(CC)CC)C.[C:45]([O:48][CH2:49][C:50](Cl)=[O:51])(=[O:47])[CH3:46]>C1COCC1.C(=O)([O-])O.[Na+]>[C:45]([O:48][CH2:49][C:50]([N:35]1[CH2:34][CH2:33][CH:32]([CH2:31][NH:30][C:28]([C:5]2[N:6]([CH3:27])[C:7]3[C:16]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[N:10]([CH2:17][C:18](=[O:25])[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:9](=[O:26])[C:8]=3[C:4]=2[O:3][CH3:2])=[O:29])[CH2:37][CH2:36]1)=[O:51])(=[O:47])[CH3:46]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 66892221HCID 66892221, compound

Product 1

HCID 57860149HCID 57860149, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of the compound of Example 542 (400 mg, 0.76 mmol) and triethylamine (0.29 mL, 2.1 mmol) in THF (17 mL) was added acetoxyacetyl chloride (0.10 mL, 0.95 mmol) under ice-cooling, and the mixture was stirred at room temperature for 4 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted twice with ethyl acetate. The extract was combined, washed with saturated brine, dried over magnesium sulfate, and filtered through aminosilica gel. The filtrate was concentrated, and the residue was recrystallized from ethanol-hexane to give the title compound (321 mg, 71%) as a white solid.

Workup

  1. temperaturecooling
  2. extractionextracted twice with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered through aminosilica gel
  6. concentrationThe filtrate was concentrated
  7. customthe residue was recrystallized from ethanol-hexane

Sources & evidence

ORD record
ord-9ae6b74a1d1f4424b0b0d97b0e3e96b5
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

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