Methanol → N6-Trityl-Lysine

HRID 1836947

반응식

HRID 1836947 반응식
Cl.Cl.[NH2:3][C@H:4]([C:10]([OH:12])=[O:11])[CH2:5][CH2:6][CH2:7][CH2:8][NH2:9].C(N(CC)CC)C.[C:20]1([C:26](Cl)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CO>ClCCl>[C:26]([NH:9][CH2:8][CH2:7][CH2:6][CH2:5][C@@H:4]([C:10]([OH:12])=[O:11])[NH2:3])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 6456Trityl chloride2회HCID 8471TriethylamineHCID 69567Lysine dihydrochloride

생성물 1

HCID 13943552N6-Trityl-Lysine수율 43%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Lysine 2HCL (1.012 g, 4.34 mmol) was suspended in 300 ml dichloromethane, and sonicated until suspension was homogeneous. Triethylamine (7.5 ml, 54.1 mmol, 2.5 eq.) was added and the mixture was left to stir for 20 minutes in Brine/Ice bath (−15° C). Triphenylmethylchloride (Trityl chloride) (6.00 g, 21.5 mmol, 1 eq.) was dissolved in 200 ml dichloromethane and then slowly added over a period of 1 hour via a dropping funnel to the reaction flask. The reaction was followed by TLC (Silica, 5% methanol/95% CH2Cl2) and was stopped 1 hour after disappearance of Trityl chloride. Volume was reduced by reduced pressure distillation. The reaction product was washed first with 5% sodium bicarbonate (2×, 20 ml each), brine (1×, 20 ml), dried over sodium sulfate, filtered, and the solvent removed at reduced pressure distillation. The product was purified by flash column chromatography (Silica Gel, 3% methanol/97% CH2Cl2) and isolated as a clear golden oil (0.753 g. Yield: 43%). 1H NMR (CDCl3, 300 MHz δ1.40 (m, 2H), 1.52 (m, 2H), 1.67 (m, 2H), 2.11 (t,2H), 3.41 (t, 1H), 3.69 (s,3H), 7.14-7.51 (m, 15H); 13C NMR (CDCl3, 75 MHz) δ23.6, 30.7, 35.0, 43.5, 51.9, 54.5, 71.0, 126.2, 127.8, 128.7, 146.4, 176.6; ESI-MS calculated for C27H30N2O2 402.53; found 403.6 [M++1].

후처리

  1. customsonicated until suspension
  2. waitthe mixture was left
  3. additionslowly added over a period of 1 hour via a dropping funnel to the reaction flask
  4. distillationVolume was reduced by reduced pressure distillation
  5. washThe reaction product was washed first with 5% sodium bicarbonate (2×, 20 ml each), brine (1×, 20 ml)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent removed at reduced pressure distillation
  9. customThe product was purified by flash column chromatography (Silica Gel, 3% methanol/97% CH2Cl2)
  10. customisolated as a clear golden oil (0.753 g. Yield: 43%)

출처 및 근거

ORD 기록
ord-c3ab0a6ec7ba4a3c9b3987c19bb7ba76
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06780856B2

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