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

HRID 406791

反応式

HRID 406791 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5e094245c1254f09b39405a0d1cdd61d
出典データセット
uspto-grants-2014_06
特許番号
US08754135B2

関連ノート

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