Dichloromethane → dibenzyl N-[N-(3-hexadecanoyloxyoctadecanoyl)-beta-alanyl]-L-glutamate

HRID 236494Notes

Reaction equation

HRID 236494 reaction equation
[C:1]([O:18][CH:19]([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][CH3:43])[CH2:20][C:21]([NH:23][CH2:24][CH2:25][C:26]([OH:28])=O)=[O:22])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C1(N=C=NC2CCCCC2)CCCCC1.ClCCl.[NH2:62][C@H:63]([C:76]([O:78][CH2:79][C:80]1[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=1)=[O:77])[CH2:64][CH2:65][C:66]([O:68][CH2:69][C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1)=[O:67]>O1CCOCC1>[C:1]([O:18][CH:19]([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][CH3:43])[CH2:20][C:21]([NH:23][CH2:24][CH2:25][C:26]([NH:62][C@H:63]([C:76]([O:78][CH2:79][C:80]1[CH:81]=[CH:82][CH:83]=[CH:84][CH:85]=1)=[O:77])[CH2:64][CH2:65][C:66]([O:68][CH2:69][C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1)=[O:67])=[O:28])=[O:22])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 3037947L-Glutamic acid dibenzyl esterHCID 20216758N-(3-hexadecanoyloxyoctadecanoyl)-beta-alanine

Product 1

HCID 54196239dibenzyl N-[N-(3-hexadecanoyloxyoctadecanoyl)-beta-alanyl]-L-glutamateYield 46.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

N-(3-hexadecanoyloxyoctadecanoyl)-β-alanine (1.47 g) prepared by the method of Preparation B-5 and N,N'-dicyclohexylcarbodiimide (412 mg) were added to a mixed solution of dichloromethane (20 ml) and dioxane (20 ml). The resulting mixture was stirred for 15 minutes. Then, a solution of dibenzyl L-glutamate (650 mg) in dioxane (10 ml) was added thereto over a period of 30 minutes. The mixture was stirred for 2 hours at room temperature and allowed to stand overnight. The precipitated N,N'-dicyclohexylurea was removed off by filtration, and the filtrate was concentrated under reduced pressure. The residue was recrystallized from ethanol to afford crystals of dibenzyl N-[N-(3-hexadecanoyloxyoctadecanoyl)-β-alanyl]-L-glutamate (850 mg).

Workup

  1. waitover a period of 30 minutes
  2. stirringThe mixture was stirred for 2 hours at room temperature
  3. waitto stand overnight
  4. customThe precipitated N,N'-dicyclohexylurea was removed off by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-e64a31668d52488fa52931eaf28f6c72
Source dataset
uspto-grants-1987_02
Patent number
US04643990

Reaction notes

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