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

HRID 363147노트

반응식

HRID 363147 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-88158683d9cb4675bd62f95e3c2f4a5b
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05872224

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