Lauric Acid → HCID 178443309, compound

HRID 846575Notes

Reaction equation

HRID 846575 reaction equation
[C:1]([OH:14])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH:15]1[CH:16]=[CH:17][C:18]([CH2:21][C@H:22]([NH:61][C:62]([CH2:64][NH:65][C:66]([C@H:68]2[N:72]([C:73]([C@H:75]3[N:79]([C:80]([C@@H:82]([NH2:90])[CH2:83][CH2:84][CH2:85][NH:86][C:87]([NH2:89])=[NH:88])=[O:81])[CH2:78][CH2:77][CH2:76]3)=[O:74])[CH2:71][CH2:70][CH2:69]2)=[O:67])=[O:63])[C:23]([NH:25][C@H:26]([C:29]([N:31]2[C@H:35]([C:36]([NH:38][C@H:39]([C:47]([NH:49][C@H:50]([C:58]([OH:60])=[O:59])[CH2:51][CH2:52][CH2:53][NH:54][C:55]([NH2:57])=[NH:56])=[O:48])[CH2:40][C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)=[O:37])[CH2:34][CH2:33][CH2:32]2)=[O:30])[CH2:27][OH:28])=[O:24])=[CH:19][CH:20]=1.N1CCCCC1.C(O)(=O)CCCCCCCCCCCCCCCCC>CO>[CH:15]1[CH:20]=[CH:19][C:18]([CH2:21][C@H:22]([NH:61][C:62]([CH2:64][NH:65][C:66]([C@H:68]2[N:72]([C:73]([C@H:75]3[N:79]([C:80]([C@@H:82]([NH2:90])[CH2:83][CH2:84][CH2:85][NH:86][C:87]([NH2:89])=[NH:88])=[O:81])[CH2:78][CH2:77][CH2:76]3)=[O:74])[CH2:71][CH2:70][CH2:69]2)=[O:67])=[O:63])[C:23]([NH:25][C@H:26]([C:29]([N:31]2[C@H:35]([C:36]([NH:38][C@H:39]([C:47]([NH:49][C@H:50]([C:58]([OH:60])=[O:59])[CH2:51][CH2:52][CH2:53][NH:54][C:55]([NH2:57])=[NH:56])=[O:48])[CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[O:37])[CH2:34][CH2:33][CH2:32]2)=[O:30])[CH2:27][OH:28])=[O:24])=[CH:17][CH:16]=1.[C:1]([O-:14])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 3893Lauric AcidHCID 5281Stearic AcidHCID 8082PiperidineHCID 178512877HCID 178512877, compound

Product 1

HCID 178443309HCID 178443309, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Lauric acid (2 g, 10 mmol) was dissolved in 80 mL of methanol in a round bottom flask; 160 mg (0.13 mmol) of bradykinin was dissolved in 10 mL methanol, and 112 mg (1.36 mmol) of piperidine was. The peptide solution was then added to the stearic acid solution and stirred for three to four hours. The solvent was evaporated by rotary evaporation; 150 mL of ether/chloroform (6:4) was added to the residue, and stirred for one hour. The mixture was filtered through a 5 μm teflon filter (Millipore Type Ls), and the solid product (85 mg) collected and dried in a vacuum dessicator. The NMR (methanol d-4) confirmed the presence of laurate at 1.3-1.4 ppm.

Workup

  1. customThe solvent was evaporated by rotary evaporation
  2. addition150 mL of ether/chloroform (6:4) was added to the residue
  3. stirringstirred for one hour
  4. filtrationThe mixture was filtered through a 5 μm teflon
  5. filtrationfilter (Millipore Type Ls)
  6. customthe solid product (85 mg) collected
  7. customdried in a vacuum dessicator

Sources & evidence

ORD record
ord-1562666b089e421caa87ff89eef0766c
Source dataset
uspto-grants-1992_08
Patent number
US05137874

Reaction notes

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