Diisopropylethylamine → ethyl (N-tert-butoxycarbonyl-6-aminohexanoyl)aminomethylsalicylate

HRID 356740ノート

反応式

HRID 356740 の反応式
Cl.NC[C:4]1[CH:5]=[C:6]([OH:15])[C:7](=[CH:13][CH:14]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH:16]([N:19](CC)C(C)C)(C)C.C1(=O)N(O[C:31](=[O:45])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])C(=O)CC1>CN(C)C=O.C(OCC)(=O)C>[C:41]([O:40][C:38]([NH:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][C:31]([NH:19][CH2:16][O:15][C:6]1[C:7](=[CH:13][CH:14]=[CH:4][CH:5]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:45])=[O:39])([CH3:42])([CH3:43])[CH3:44]

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 5074016Boc-6-Ahx-OSuHCID 12794728Ethyl 4-aminomethylsalicylate hydrochloride

生成物 1

HCID 53930957ethyl (N-tert-butoxycarbonyl-6-aminohexanoyl)aminomethylsalicylate収率 128.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Ethyl 4-aminomethylsalicylate hydrochloride (0.52 g, 1.28 mmoles) was suspended in anhydrous N,N-dimethylformamide (25 mL), and N,N-diisopropylethylamine (0.79 mL, 4.53 mmoles) was added, followed by N-tert-butoxycarbonyl-6-aminohexanoic acid succinimidyl ester (0.74 g, 2.26 mmoles). The mixture was stirred under dry nitrogen for 18 hours, during which time all solids dissolved. The reaction mixture was diluted with ethyl acetate (100 mL) and extracted with 1N aqueous hydrochloric acid (100 mL). The layers were separated, and the ethyl acetate solution was washed with water (100 mL) and saturated aqueous sodium chloride (500 mL). The ethyl acetate solution was dried over anhydrous magnesium sulfate, filtered, and evaporated to afford an amorphous off-white solid. Finally, the solid was crystallized from ethyl acetate, filtered, and dried in vacuo to afford 0.67 g (73% yield) of ethyl (N-tert-butoxycarbonyl-6-aminohexanoyl)aminomethylsalicylate (m.p. 120°-121° C., open capillary, uncorrected).

後処理

  1. dissolutiondissolved
  2. extractionextracted with 1N aqueous hydrochloric acid (100 mL)
  3. customThe layers were separated
  4. washthe ethyl acetate solution was washed with water (100 mL) and saturated aqueous sodium chloride (500 mL)
  5. dry with materialThe ethyl acetate solution was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto afford an amorphous off-white solid
  9. customFinally, the solid was crystallized from ethyl acetate
  10. filtrationfiltered
  11. customdried in vacuo

出典と根拠

ORDレコード
ord-0293cefcb6ce432da05486c3c91dbbc7
出典データセット
uspto-grants-1998_11
特許番号
US05837878

反応ノート

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