4-Methylmorpholine → HCID 10724280, compound

HRID 636314

Reaction equation

HRID 636314 reaction equation
[C:1]1(CCCC(O)=O)[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.[CH3:23][N:24]1[CH2:29][CH2:28]O[CH2:26][CH2:25]1.[CH:30]1(N=C=NC2CCCCC2)[CH2:35]CCC[CH2:31]1.[OH:45]N1C2C=CC=CC=2N=N1.[N+:55]([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=1[S:64]([N:67]1[CH2:81]CNCCC[N:75]([S:82]([C:85]2[CH:90]=[CH:89][CH:88]=[CH:87][C:86]=2[N+:91]([O-:93])=[O:92])(=[O:84])=[O:83])[CH2:74][C:73]2[N:94]=[C:69]([CH:70]=[CH:71][CH:72]=2)[CH2:68]1)(=[O:66])=[O:65])([O-:57])=[O:56]>C(Cl)Cl>[C:1]1([CH2:31][CH2:30][CH2:35][C:23]([N:24]2[CH2:29][CH2:28][CH2:81][N:67]([S:64]([C:59]3[CH:60]=[CH:61][CH:62]=[CH:63][C:58]=3[N+:55]([O-:57])=[O:56])(=[O:65])=[O:66])[CH2:68][C:69]3[N:94]=[C:73]([CH:72]=[CH:71][CH:70]=3)[CH2:74][N:75]([S:82]([C:85]3[CH:90]=[CH:89][CH:88]=[CH:87][C:86]=3[N+:91]([O-:93])=[O:92])(=[O:83])=[O:84])[CH2:26][CH2:25]2)=[O:45])[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 769771-Pyrenebutanoic acidHCID 10555399HCID 10555399, compound

Product 1

HCID 10724280HCID 10724280, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-pyrenebutyric acid (0.87 g, 3.0 mmol) and 4-methylmorpholine (0.59 g, 5.9 mmol) in 20 mL of anhydrous CH2Cl2 was stirred at rt for 30 min. After addition of 1,3-dicyclohexylcarbodiimide (DCC) (0.62 g, 3.0 mmol) and 1-hydroxybenzotriazole (HOBT) (0.41 g, 3.0 mmol), the resulting solution was stirred at rt for another 30 min. A solution of 3,10-bis(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1(16),12,14-triene (from Example 72, 1.77 g, 3.0 mmol) was added to the above solution and the resulting solution was stirred at rt for 40 h. The solution was filtered and the filtrate was washed with brine , dried (Na2SO4) and concentrated. The residue was purified by flash chromatography on a silica gel column using 100:1 CH2Cl2—MeOH as an eluent to give 2.36 g (92%) of the title compound as a pale yellow foam.

Workup

  1. stirringthe resulting solution was stirred at rt for another 30 min
  2. stirringthe resulting solution was stirred at rt for 40 h
  3. filtrationThe solution was filtered
  4. washthe filtrate was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on a silica gel column

Sources & evidence

ORD record
ord-687c2ab313534964ac1e145c8309a1e3
Source dataset
uspto-grants-2001_02
Patent number
US06191273B1

Linked notes

Loading…