Formaldehyde → HCID 10401484, 화합물

HRID 2245782노트

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HRID 2245782 반응식
[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9][C:10]1[CH:15]=[CH:14][C:13](N)=[CH:12][CH:11]=1.[CH2:18]=O.[C:20]([BH3-])#[N:21].[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9][C:10]1[CH:15]=[CH:14][C:13]([N:21]([CH3:20])[CH3:18])=[CH:12][CH:11]=1

참가 물질

6

반응물 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 11777044Hexanoic acid, 6-[(4-aminophenyl)thio]-, methyl ester

생성물 1

HCID 10401484HCID 10401484, 화합물수율 79%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 887Methanol용매2회

실험 절차

To a solution of 6-(4-amino-phenylsulfanyl)-hexanoic acid methyl ester (2.5 g, 10 mmol) in methanol (20 mL) was added at 0° C. a 37% aqueous solution of formaldehyde (2.4 mL, 30 mmol) and a solution of sodium cyanoborohydride (2.5 g, 40 mmol) and zinc chloride (2.7 g, 20 mmol) in methanol (150 mL). The mixture was stirred at room temperature for 2 hours and concentrated under reduced pressure. The residue was taken up in ethyl acetate (250 mL) and aqueous sodium hydroxide (100 mL, 2M). The organic layer was washed consecutively with aqueous sodium hydroxide (100 mL, 2M), distilled water (2×100 mL) and brine (2×100 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give a yellow oil that was purified by flash chromatography (10:90:1 to 20:80:1 ethyl acetate:40-60° C. petroleum ether:triethylamine) to give the title compound (2.2 g, 79%) as a colourless oil.

후처리

  1. concentrationconcentrated under reduced pressure
  2. washThe organic layer was washed consecutively with aqueous sodium hydroxide (100 mL, 2M)
  3. distillationdistilled water (2×100 mL) and brine (2×100 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a yellow oil that
  8. customwas purified by flash chromatography (10:90:1 to 20:80:1 ethyl acetate:40-60° C. petroleum ether:triethylamine)

출처 및 근거

ORD 기록
ord-495d6e46c5384ed2a0e490168090c0fa
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07683185B2

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