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Acetic Acid → N6-(1-Oxohexadecyl)-L-lysine

HRID 728239
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HRID 728239 반응식
[C:1]([OH:18])(=O)[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].Cl.[NH2:20][C@H:21]([C:27]([OH:29])=[O:28])[CH2:22][CH2:23][CH2:24][CH2:25][NH2:26].C(N(CC)CC)C.C(O)(=O)C>CC(C)=O.O>[O:18]=[C:1]([NH:26][CH2:25][CH2:24][CH2:23][CH2:22][C@@H:21]([C:27]([OH:29])=[O:28])[NH2:20])[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 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 985Palmitic AcidHCID 8471TriethylamineHCID 69568L-Lysine monohydrochloride

생성물 1

HCID 100425N6-(1-Oxohexadecyl)-L-lysine수율 73%

시약·촉매·용매 2

HCID 180Acetone용매
HCID 962
Water
용매
2회

실험 절차

Following the procedure of A. Paquet Can. J. Chem. 54, 733 (1976), 353 mg. (1 mmol) of the succinimidylester of hexadecanoic acid, prepared as in example 2, was suspended in 2 ml acetone and added to a solution of 183 mg (1 mmol) L-lysine hydrochloride and 0.27 ml (ca. 2 mmol) triethylamine in 2 ml water. The reaction mixture was stirred vigorously for at least 4 h, then neutralized with acetic acid and diluted with water. The precipitate was removed by filtration and washed with water, methanol and ether. Repeated crystallizations from acetic acid/water and acetic acid gave 280 mg (73%) colourless crystals, m.p. 240°-245° C. (reported 210°-220° C.)

후처리

  1. customThe precipitate was removed by filtration
  2. washwashed with water, methanol and ether
  3. customcrystallizations from acetic acid/water and acetic acid

출처 및 근거

ORD 기록
ord-412eac3935a74c7f8adb0d2fa1c6d42c
출처 데이터셋
uspto-grants-1991_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05047535

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