Hydroxyamine hydrochloride → HCID 10154708、化合物

HRID 1362553ノート

反応式

HRID 1362553 の反応式
C[O-].[Na+].Cl.[NH2:5][OH:6].C[O:8][C:9](=O)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:30])/[CH:17]=[CH:18]/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N+:27]([O-:29])=[O:28]>CO>[OH:6][NH:5][C:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:30])/[CH:17]=[CH:18]/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N+:27]([O-:29])=[O:28])=[O:8]

参加物

5

反応物 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 57495376HCID 57495376、化合物

生成物 1

HCID 10154708HCID 10154708、化合物収率 66.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

A solution of sodium methylate (6.0 mmol) in methanol (5 ml) was added to a solution of hydroxylamine hydrochloride (0.28 g, 4.0 mmol) (Acros) in methanol (8 ml). The mixture was stirred for 10 min. and the precipitate was filtered off. (2E,4E)-6-[5-(2-Nitrophenyl)penta-2,4-dienoylamino]hexanoic acid methyl ester (13a) (0.35 g, 1 mmol) was added to the filtrate and the obtained mixture was heated to the complete dissolving. The resultant mixture was stirred for 4 hours at ambient temperature and the solvent was removed under reduced pressure. The product was dissolved in water (10 ml) and the solution was acidified with 3% HCl. The precipitate was filtered and crystallized from acetonitrile to give the title compound (0.23 g, 66%) as a yellow solid. M.p. 131-133° C. 1H NMR (DMSO-d6, HMDSO), δ: 1.06-1.73 (6H, m, CH2); 1.87-2.09 (2H, m, CH2); 3.15 (2H, q, J=5.6 Hz, CH2N); 6.26 (1H, d, J=14.8 Hz, CH); 7.00-8.06 (8H, m, CH—CH═CH, C6H4, NH); 8.06 (1H, t, J=5.9 Hz, NH); 10.33 (1H, s, OH). HPLC analysis on Symmetry C18 column: impurities <1.0% (column size 3.9×150 mm; mobile phase acetonitrile −0.1 M phosphate buffer (pH 2.5), 35:65; detector UV 220 nm; sample concentration 0.15 mg/ml). Anal. Calcd for C17H21N3O5, %: 58.78, H, 6.09, N, 12.10. Found, %: C, 58.26, H, 6.08, N, 11.87.

後処理

  1. filtrationthe precipitate was filtered off
  2. temperaturethe obtained mixture was heated to the complete dissolving
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe product was dissolved in water (10 ml)
  5. filtrationThe precipitate was filtered
  6. customcrystallized from acetonitrile

出典と根拠

ORDレコード
ord-0d2d3d1ac2474c51925b02af0271d1f0
出典データセット
uspto-grants-2011_02
特許番号
US07880020B2

反応ノート

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