Triethylamine → Ethyl 5-(aminomethyl)isoxazole-3-carboxylate, 5-BOC protected

HRID 2111674노트

반응식

HRID 2111674 반응식
[CH3:1][CH2:2][O:3][C:4](/[C:6](/Cl)=[N:7]\[OH:8])=[O:5].[C:10]([O:14][C:15]([NH:17][CH2:18][C:19]#[CH:20])=[O:16])([CH3:13])([CH3:12])[CH3:11].C(N(CC)CC)C>C1COCC1>[CH2:2]([O:3][C:4]([C:6]1[CH:20]=[C:19]([CH2:18][NH:17][C:15]([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:16])[O:8][N:7]=1)=[O:5])[CH3:1]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 6399471Ethyl 2-chloro-2-(hydroxyimino)acetateHCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamate

생성물 1

HCID 10588096Ethyl 5-(aminomethyl)isoxazole-3-carboxylate, 5-BOC protected수율 60%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of ethyl chlorooximidoacetate (10 g, 66 mmol) in THF (200 ml) was added dropwise over 3 hours to a mixture of N-(tert-butyloxycarbonyl)propargylamine (20.5 g, 131 mmol) and triethylamine (11.2 ml, 80 mmol) in tetrahyrofuran (100 ml). The mixture was stirred at ambient temperature for 18 hours and then the volatiles were removed by evaporation. The residue was dissolved in DCM and washed with water followed by brine. The organics were separated, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography on silica gel eluting with isohexane/diethyl ether (80:20 then 50:50) to give the title compound (10.6 g, 60%). NMR (DMSO): 1.3 (t, 3H), 1.38 (s, 9H), 4.35 (m, 2H), 6.62 (s, 1H), 7.55 (s, 1H); m/z 269 (M−H)—.

후처리

  1. customthe volatiles were removed by evaporation
  2. dissolutionThe residue was dissolved in DCM
  3. washwashed with water
  4. customThe organics were separated
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed by evaporation
  7. customThe residue was purified by column chromatography on silica gel eluting with isohexane/diethyl ether (80:20

출처 및 근거

ORD 기록
ord-7f84297867654b40b98f3ebe1f43cae8
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07521453B2

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