Hydrochloric Acid → N-[3-(Hexadecanoyloxy)octadecanoyl]-L-valine

HRID 236481

반응식

HRID 236481 반응식
[C:1]([O:18][CH:19]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:20][C:21]([OH:23])=O)(=[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].ON1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:62][C@H:63]([C:67]([OH:69])=[O:68])[CH:64]([CH3:66])[CH3:65].Cl>O1CCOCC1.CN(C)C=O.O.C(N(CC)CC)C>[C:1]([O:18][CH:19]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:20][C:21]([NH:62][C@H:63]([C:67]([OH:69])=[O:68])[CH:64]([CH3:66])[CH3:65])=[O:23])(=[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]

참가 물질

10

반응물 5

HCID 313Hydrochloric AcidHCID 6287L-ValineHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 134890283-Hexadecanoyloxyoctadecanoic acid

생성물 1

HCID 53729937N-[3-(Hexadecanoyloxy)octadecanoyl]-L-valine수율 62.6%

시약·촉매·용매 4

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매HCID 312751,4-Dioxane용매

실험 절차

3-Hexadecanoyloxyoctadecanoic acid (10.8 g) prepared by the method described in Preparation A-2 (5) and N-hydroxysuccinimide (2.3 g) was dissolved in dioxane (60 ml). N,N'-Dicyclohexylcarbodiimide (4.2 g) was added thereto under ice cooling. The mixture was stirred at ambient temperature over-night. The crystallized N,N'-dicyclohexylurea was filtered off and the filtrate was concentrated to give a residue. The residue was dissolved in N,N-dimethylformamide (70 ml). To this solution was added a solution of L-valine (5.85 g) and triethylamine (6.95 ml) in water (50 ml) at 0° C. The resulting mixture was stirred at ambient temperature overnight. The reaction mixture was acidified with 1N hydrochloric acid, extracted with ethyl acetate, washed with water and dried over magnesium sulfate. Ethyl acetate was distilled off to give a residue which was crystallized from petroleum ether to give crystals of N-(3-hexadecanoyloxyoctadecanoyl)-L-valine (8 g).

후처리

  1. filtrationThe crystallized N,N'-dicyclohexylurea was filtered off
  2. concentrationthe filtrate was concentrated
  3. customto give a residue
  4. stirringThe resulting mixture was stirred at ambient temperature overnight
  5. extractionextracted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationEthyl acetate was distilled off
  9. customto give a residue which
  10. customwas crystallized from petroleum ether

출처 및 근거

ORD 기록
ord-8f9b83e64f3f4693b46e3b73e9a3fec2
출처 데이터셋
uspto-grants-1987_02
특허 번호
US04643990

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