Nitrogen → HCID 67365195、化合物

HRID 42873ノート

反応式

HRID 42873 の反応式
N#N.[Cl:3][C:4]1[CH:28]=[CH:27][CH:26]=[CH:25][C:5]=1[CH2:6][O:7][C:8](=[O:24])[NH:9][C:10]1[CH:14]=[N:13][N:12]([CH2:15][C:16]2[N:17]=[C:18]([CH:21](O)[OH:22])[O:19][CH:20]=2)[N:11]=1.[CH3:29][Mg]Br.[NH4+].[Cl-]>C1COCC1>[Cl:3][C:4]1[CH:28]=[CH:27][CH:26]=[CH:25][C:5]=1[CH2:6][O:7][C:8](=[O:24])[NH:9][C:10]1[CH:14]=[N:13][N:12]([CH2:15][C:16]2[N:17]=[C:18]([CH:21]([OH:22])[CH3:29])[O:19][CH:20]=2)[N:11]=1

参加物

6

反応物 4

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 67365246[2-(2-dihydroxymethyl-oxazol-4-ylmethyl)-2H-[1,2,3]triazol-4-yl]-carbamic acid 2-chloro-benzyl esterHCID 178418573HCID 178418573、化合物

生成物 1

HCID 67365195HCID 67365195、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-65 °C

実験手順

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [2-(2-dihydroxymethyl-oxazol-4-ylmethyl)-2H-[1,2,3]triazol-4-yl]-carbamic acid 2-chloro-benzyl ester (19 mg, 0.05 mmol) in THF (1.0 mL) was treated at −65° C. with methylmagnesium bromide (0.15 mL of a 1M solution in THF, 0.15 mmol). The reaction mixture was then stirred at −65° C. for 1 h. The reaction mixture was then slowly warmed to rt and stirred at this temperature for 45 min. Sat. aq. NH4Cl was then added and the aq. layer was extracted with EA (3×10 mL). The combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. The residue was purified by FC (EA) to give the title compound as a yellow oil. TLC: rf (EA)=0.30. LC-MS-conditions 02: tR=0.89 min, [M+H]+=378.30.

後処理

  1. temperatureThe reaction mixture was then slowly warmed to rt
  2. stirringstirred at this temperature for 45 min
  3. extractionthe aq. layer was extracted with EA (3×10 mL)
  4. dry with materialextracts were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customThe residue was purified by FC (EA)

出典と根拠

ORDレコード
ord-6fed5a318e824a0abf35ecd30694f39d
出典データセット
uspto-grants-2013_09
特許番号
US08536209B2

反応ノート

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