Methanol → 4-Azido-5-methyl-1-(pyridine-2-sulfonyl)-azepan-3-ol

HRID 1790602

反応式

HRID 1790602 の反応式
C[CH:2]1[CH2:9][CH:8]2[CH:6]([O:7]2)[CH2:5][N:4]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)(=[O:12])=[O:11])[CH2:3]1.[N-:19]=[N+:20]=[N-:21].[Na+].[NH4+].[Cl-].[CH3:25]O>O>[N:19]([CH:8]1[CH:9]([CH3:25])[CH2:2][CH2:3][N:4]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)(=[O:11])=[O:12])[CH2:5][CH:6]1[OH:7])=[N+:20]=[N-:21]

参加物

6

反応物 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 220366865-Methyl-3-(pyridine-2-sulfonyl)-8-oxa-3-aza-bicyclo[5.1.0]octane

生成物 1

HCID 220366394-Azido-5-methyl-1-(pyridine-2-sulfonyl)-azepan-3-ol収率 64%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

5-methyl-3-(pyridine-2-sulfonyl)-8-oxa-3-aza-bicyclo[5.1.0]octane (230 mg, 0.86 mmol) was dissolved in the mixture of 8 ml MeOH and 2 ml H2O. NaN3 (170 mg, 2.6 mmol) and NH4Cl (140 mg, 2.6 mmol) were added to the solution. The resulting mixture was refluxed overnight. After the removal of MeOH, the residue was diluted in EtOAc and washed with 10% NaHCO3 and brine. Purified on column chromatography gave the title compound (170 mg, yield 64%). MS (M+H+) 312.2; 1H-NMR (400 Hz, CDCl3): d=8.69(d, 1H), 8.04–7.94(m, 2H), 7.54 (m, 1H) 4.00–2.95 (m, 7H), 2.20(m, 1H), 1.90–1.74(m, 2H), 0.98(d, 3H).

後処理

  1. temperatureThe resulting mixture was refluxed overnight
  2. customAfter the removal of MeOH
  3. additionthe residue was diluted in EtOAc
  4. washwashed with 10% NaHCO3 and brine
  5. customPurified on column chromatography

出典と根拠

ORDレコード
ord-7aa9cdfe43284d549adfbad416cbc22d
出典データセット
uspto-grants-2006_07
特許番号
US07071184B2

関連ノート

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