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

HRID 363147ノート

反応式

HRID 363147 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-88158683d9cb4675bd62f95e3c2f4a5b
出典データセット
uspto-grants-1999_02
特許番号
US05872224

反応ノート

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