Octadecylamine → HCID 69592655, compound

HRID 1822610Notes

Reaction equation

HRID 1822610 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([C:24]([OH:26])=O)[C@H:20]([CH2:22][CH3:23])[CH3:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:27]([NH2:45])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44].Cl.C(N=C=NCCCN(C)C)C>CN(C1C=CN=CC=1)C.ClCCl>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([C:24]([NH:45][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])=[O:26])[C@H:20]([CH2:22][CH3:23])[CH3:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 15793OctadecylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2724629N-Fmoc-L-isoleucine

Product 1

HCID 69592655HCID 69592655, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2.47 g (0.007 mol) of N-[(9-fluorenyl)methoxycarbonyl]-L-isoleucine, 1.89 g (0.007 mol) of octadecylamine, 85.5 mg (0.0007 mol) of 4-(N,N-dimethylamino)pyridine (DMAP), and 1.61 g (0.0084 mol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) was dissolved in 45 ml of dichloromethane, and the resultant solution was stirred for 4 days at room temperature. Then, the obtained reaction mixture was extracted with dichloromethane, and the organic layer was dried over anhydrous magnesium sulfate. Thereafter, the solvent was distilled off under reduced pressure, the resultant residue was subjected to re-crystallization treatment using ethyl acetate, and gel-like substance was subjected to a suction filtration, thereby obtaining 3.69 g of N-[(9-fluorenyl)methoxycarbonyl]-L-isoleucylaminooctadecane (hereinafter also referred to as “Intermediate product (1)”) at the yield of 87%.

Workup

  1. customThen, the obtained reaction mixture
  2. extractionwas extracted with dichloromethane
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. distillationThereafter, the solvent was distilled off under reduced pressure
  5. customthe resultant residue was subjected to re-crystallization treatment
  6. filtrationwas subjected to a suction filtration

Sources & evidence

ORD record
ord-f6af6587c2b6444a802684fc0cce1da6
Source dataset
uspto-grants-2006_05
Patent number
US07037444B2

Reaction notes

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