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

HRID 236481

反応式

HRID 236481 の反応式
[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]

参加物

10

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8f9b83e64f3f4693b46e3b73e9a3fec2
出典データセット
uspto-grants-1987_02
特許番号
US04643990

関連ノート

読み込み中…