Triethylamine → HCID 136404631, compound

HRID 613349Notes

Reaction equation

HRID 613349 reaction equation
Cl.[N:2]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH:6]=[CH:5][N:4]=[CH:3]1.C(N(CC)CC)C.O[CH2:25][C:26]1[CH:30]=[C:29]2[C:31]([C:89]3[CH:94]=[CH:93][CH:92]=[CH:91][C:90]=3[NH:95][C:96](=[O:101])[C:97]([CH3:100])([CH3:99])[CH3:98])=[C:32]3[N:36]=[C:35]([C:37]([C:76]4[CH:81]=[CH:80][CH:79]=[CH:78][C:77]=4[NH:82][C:83](=[O:88])[C:84]([CH3:87])([CH3:86])[CH3:85])=[C:38]4[NH:42][C:41](=[C:43]([C:63]5[CH:68]=[CH:67][CH:66]=[CH:65][C:64]=5[NH:69][C:70](=[O:75])[C:71]([CH3:74])([CH3:73])[CH3:72])[C:44]5[CH:45]=[CH:46][C:47](=[C:49]([C:50]6[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=6[NH:56][C:57](=[O:62])[C:58]([CH3:61])([CH3:60])[CH3:59])[C:27]=1[NH:28]2)[N:48]=5)[CH:40]=[CH:39]4)[CH:34]=[CH:33]3.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C.CN(C1C=CN=CC=1)C>[N:2]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:25][C:26]2[CH:30]=[C:29]3[C:31]([C:89]4[CH:94]=[CH:93][CH:92]=[CH:91][C:90]=4[NH:95][C:96](=[O:101])[C:97]([CH3:100])([CH3:99])[CH3:98])=[C:32]4[N:36]=[C:35]([C:37]([C:76]5[CH:81]=[CH:80][CH:79]=[CH:78][C:77]=5[NH:82][C:83](=[O:88])[C:84]([CH3:87])([CH3:85])[CH3:86])=[C:38]5[NH:42][C:41](=[C:43]([C:63]6[CH:68]=[CH:67][CH:66]=[CH:65][C:64]=6[NH:69][C:70](=[O:75])[C:71]([CH3:72])([CH3:73])[CH3:74])[C:44]6[CH:45]=[CH:46][C:47](=[C:49]([C:50]7[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=7[NH:56][C:57](=[O:62])[C:58]([CH3:59])([CH3:60])[CH3:61])[C:27]=2[NH:28]3)[N:48]=6)[CH:40]=[CH:39]5)[CH:34]=[CH:33]4)=[O:15])[CH:6]=[CH:5][N:4]=[CH:3]1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 10868DicyclohexylcarbodiimideHCID 12870425HCID 12870425, compoundHCID 136404630HCID 136404630, compound

Product 1

HCID 136404631HCID 136404631, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

8-Imidazol-1-yloctanoic acid hydrochloride (90.1 mg, 0.37 mmol) and triethylamine (TEA, 0.1 ml, 0.74 mmol) were dissolved in dry DMF (4 ml) and stirred for 10 min. After removing TEA under reduced pressure, 2-hydroxymethyl-5,10,15,20-tetrakis(o-pivalamidophenyl)porphyrin, 76 mg, 73 μmol), 4-(N,N-dimethylamino)pyridine (DMAP, 4.5 mg, 37 μmol) and dicyclohexylcarbodiimide (DCC, 75.4 mg, 0.37 mmol) were added to the solution and stirred for 84 hours at room temperature in darkness. The mixture was chromatographed on a silica gel flash column using CHCl3 --MeOH (30/1 v/v) as the eluent. The residue was dried at room temperature in vacuo to give a purple product, 2-(8-imidazol-1-yloctanoyloxymethyl)-5,10,15,20-tetrakis(o-pivalamidophenyl)porphyrin (80 mg, 89%).

Workup

  1. additionwere added to the solution
  2. stirringstirred for 84 hours at room temperature in darkness
  3. customThe mixture was chromatographed on a silica gel flash column
  4. customThe residue was dried at room temperature in vacuo

Sources & evidence

ORD record
ord-be0803a4a1f34b0198d2786248d524a6
Source dataset
uspto-grants-1999_12
Patent number
US06008198

Reaction notes

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