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Ethyl Acetate → N-(2-Amino-6-methylpyridin-3-ylmethyl)-N-(4-hydroxy-1-methyl-2-propyldisulfanylbut-1-enyl)formamide

HRID 1360833
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HRID 1360833 반응식
[NH2:1][C:2]1[C:7]([CH2:8][N:9]([C:12]([CH3:37])=[C:13](SSC(CCO)=C(NC(CC2C(N)=NC(C)=CC=2)=O)C)[CH2:14][CH2:15][OH:16])[CH:10]=[O:11])=[CH:6][CH:5]=[C:4]([CH3:38])[N:3]=1.[CH2:39]([S:42][S:43]CCC)[CH2:40][CH3:41].[OH-].[Na+].C(OCC)(=O)C>CO.O.C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:7]([CH2:8][N:9]([C:12]([CH3:37])=[CH:13][CH2:14][CH:15]([S:43][S:42][CH2:39][CH2:40][CH3:41])[OH:16])[CH:10]=[O:11])=[CH:6][CH:5]=[C:4]([CH3:38])[N:3]=1
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참가 물질

8

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HCID 8857Ethyl AcetateHCID 12377Dipropyl disulfideHCID 14798Sodium HydroxideHCID 86616941N-(2-amino-6-methylpyridin-3-ylmethyl)-N-{2-[2-[(2-amino-6-methyl-pyridin-3-ylmethyl)formylamino]-1-(2-hydroxyethyl)-propenyldisulfanyl]-4-hydroxy-1-methylbut-1-enyl}formamide

생성물 1

HCID 86616940N-(2-Amino-6-methylpyridin-3-ylmethyl)-N-(4-hydroxy-1-methyl-2-propyldisulfanylbut-1-enyl)formamide
수율 81.3%

시약·촉매·용매 3

HCID 887Methanol용매2회HCID 962Water용매HCID 6212Chloroform용매

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온도
40 °C

실험 절차

To a solution of N-(2-amino-6-methylpyridin-3-ylmethyl)-N-{2-[2-[(2-amino-6-methyl-pyridin-3-ylmethyl)formylamino]-1-(2-hydroxyethyl)-propenyldisulfanyl]-4-hydroxy-1-methylbut-1-enyl}formamide (250 mg, 0.45 mmol) and propyl disulfide (0.21 mL, 1.34 mmol) in methanol (3 ml) was added 1 molar aqueous sodium hydroxide (0.089 mL, 0.089 mmol). The resulting solution was stirred at 35-45° C. for 18 hr. The solution was diluted with water (10 mL) and chloroform (10 mL), but the product remained as a milky insoluble layer. Addition of ethyl acetate (10 mL) and methanol (2 mL) resulted in the formation of two clear layers. The product was contained in the lower layer. This layer was washed with brine (10 mL) dried over sodium sulfate, and evaporated. The residual oil was dissolved in chloroform (1 mL) and chromatographed on silica gel (Waters Sep-Pak 5 g column, using 97.5/2.5 chloroform/methanol as eluent, Fraction size 9 mL). Fractions 4-9 were pooled and evaporated to give 130 mg (41%) of the title compound as nearly colorless oil. MS (LCMS): 356.0 (M+H)+. 1H NMR (CDCl3) δ 0.95 (t, 3H), 1.55 (m, 3H), 1.97 (s, 3H), 2.35 (s, 3H), 2.42 (t, 2H), 2.84 (t, 2H) 3.76 (t, 2H), 5.36 (br. s, 1H), 6.35 (d, 1H), 7.02 (d, 1H), 7.96 (s, 1H).

후처리

  1. customresulted in the formation of two clear layers
  2. washThis layer was washed with brine (10 mL)
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. dissolutionThe residual oil was dissolved in chloroform (1 mL)
  6. customchromatographed on silica gel (Waters Sep-Pak 5 g column, using 97.5/2.5 chloroform/methanol as eluent, Fraction size 9 mL)
  7. customevaporated

출처 및 근거

ORD 기록
ord-d24d588c57824ce5a9a788ce8ddbb71f
출처 데이터셋
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07879885B2

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