Triethylamine → 2,6-Bis-(2-benzyloxy-acetylamino)-hexanoic acid methyl ester

HRID 383199

반응식

HRID 383199 반응식
Cl.Cl.[CH3:3][O:4][C:5](=[O:13])[C@H:6]([CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])[NH2:7].C(N([CH2:19][CH3:20])CC)C.[CH2:21]([O:28][CH2:29][C:30](Cl)=[O:31])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(OCC)(=O)C>[CH3:3][O:4][C:5](=[O:13])[CH:6]([NH:7][C:30](=[O:31])[CH2:29][O:28][CH2:21][C:20]1[CH:19]=[CH:24][CH:23]=[CH:22][CH:27]=1)[CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:30](=[O:31])[CH2:29][O:28][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 117778Methyl L-lysinate dihydrochlorideHCID 177085Benzyloxyacetyl chloride

생성물 1

HCID 596824872,6-Bis-(2-benzyloxy-acetylamino)-hexanoic acid methyl ester수율 31.8%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of L-lysine methyl ester dihydrochloride (50 grams, 214.4 mmol), triethylamine (131 grams, 1.294 moles) in ethyl acetate (750 mL) at room temperature was added benzyloxy acetyl chloride (120 grams, 650.4 mmol) drop wise. The mixture was further stirred at room temperature for 2 hours. The solids were filtered off. The organic phase was washed with 5% sodium bicarbonate (2×100 mL), water (2×100 mL), dried over sodium sulphate and distilled. The crude 2 was purified by column chromatography on silica gel using Benzene: Ethyl acetate (9:1) to get pure 2 (30 grams, 31.8%) as a white powder.

후처리

  1. filtrationThe solids were filtered off
  2. washThe organic phase was washed with 5% sodium bicarbonate (2×100 mL), water (2×100 mL)
  3. dry with materialdried over sodium sulphate
  4. distillationdistilled
  5. customThe crude 2 was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-eafcc244dfa248c5ba85114b659eccac
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367108B2

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