3-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]propoxyamine → 3-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]propanol Hydrochloride

HRID 1059462ノート

反応式

HRID 1059462 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([CH:22]=[C:23]([CH3:25])[CH:24]=1)[O:16][CH2:17][CH2:18][CH2:19][O:20]N)(=[O:11])=[O:10])#[N:2].[ClH:26].N1C=CC(C(N)=N)=N1>CN(C)C=O>[ClH:26].[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([CH:22]=[C:23]([CH3:25])[CH:24]=1)[O:16][CH2:17][CH2:18][CH2:19][OH:20])(=[O:11])=[O:10])#[N:2]

参加物

4

反応物 2

HCID 227225313-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]propoxyamineHCID 178479321HCID 178479321、化合物

生成物 1

HCID 186697053-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]propanol Hydrochloride収率 88.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

3-[13-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]propoxy guanidine hydrochloride: To a solution of 3-[3-(2-cyanophenylsulfonyloxy)-5-methylphenoxy] propoxyamine (362 mg, 1.0 mmol), as prepared in the preceding step, in N,N-dimethylformamide (10 mL) was added 1H-pyrazole-carboxamidine hydrochloride (590 mg, 4.0 mmol). The reaction mixture was stirred at ambient temperature for two days. N,N-Dimethylformamide was removed under high vacuum. Acetonitrile (10 mL) was added, the solid was removed by filtration, the filtrate was concentrated in vacuo, and the residue was dried under high vacuum. The residue was partitioned between water (30 mL plus 2 mL brine) and diethyl ether (20 mL). The water solution was extracted with diethyl ether (20 mL), and the combined diethyl ether extracts were extracted with acidic water (pH 5). The combined water solutions were adjusted to pH 8-9 by using 2N NaOH and extracted with ethyl acetate (3×50 mL). The ethyl acetate solution was washed with pH 7 buffer solution (2×30 mL) and brine (30 mL) and dried over Na2SO4. After removing the solvent. 0.6 N HCl methanol (10 mL) was added, and the solution was concentrated to give the title compound as a colorless oil (340 mg, 77%). 1H-NMR (300 MHz, DMSO-d6) δ 8.30 (d, J=7.5 Hz, 1H), 8.09 (t, J=7.5 Hz, 1H), 8.04 (m, 2H), 7.72 (br s, 5H), 6.79 (s, 1H), 6.49 (s, 1H), 6.47 (s, 1H), 3.99 (t, J=6.2 Hz, 2H), 3.90 (t, J=6.3 Hz, 2H), 2.22 (s, 3H), 2.01 (m, 2H). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C18H20N4O5S: 405.1 (M+H), 427.1 (M+Na). Found: 405.1, 427.0.

後処理

  1. customN,N-Dimethylformamide was removed under high vacuum
  2. additionAcetonitrile (10 mL) was added
  3. customthe solid was removed by filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe residue was dried under high vacuum
  6. customThe residue was partitioned between water (30 mL plus 2 mL brine) and diethyl ether (20 mL)
  7. extractionThe water solution was extracted with diethyl ether (20 mL)
  8. extractionthe combined diethyl ether extracts were extracted with acidic water (pH 5)
  9. extractionextracted with ethyl acetate (3×50 mL)
  10. washThe ethyl acetate solution was washed with pH 7 buffer solution (2×30 mL) and brine (30 mL)
  11. dry with materialdried over Na2SO4
  12. customAfter removing the solvent
  13. addition0.6 N HCl methanol (10 mL) was added
  14. concentrationthe solution was concentrated

出典と根拠

ORDレコード
ord-6acf45b3ca7645f5aadd10c598a3dacc
出典データセット
uspto-grants-2003_02
特許番号
US06518310B2

反応ノート

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