Hydroxylamine → HCID 9819974、化合物

HRID 2084936ノート

反応式

HRID 2084936 の反応式
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH:16]2[C:21]([OH:23])=O)(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].CN(C=O)C.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[NH2:42][OH:43]>ClCCl.C1COCC1>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH:16]2[C:21]([NH:42][OH:43])=[O:23])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

参加物

8

反応物 5

HCID 787HydroxylamineHCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22644786HCID 22644786、化合物

生成物 1

HCID 9819974HCID 9819974、化合物収率 77.8%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of 4-([4-(2-butynyloxy)phenyl]sulfonyl}-morpholine-3-carboxylic acid (0.52 g, 1.53 mmol) and DMF (0.24 mL, 3.1 mmol) in dichloromethane (6 mL) was cooled in an ice bath and oxalyl chloride (1.54 mL of 2M in CH2Cl2; 3.1 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 10 minutes and at room temperature for 2 hours and then recooled to 0°. A THF (4.5 mL) solution of triethyl amine (0.86 mL, 6.13 mmol) and hydroxylamine (0.56 mL of 50% hydroxyamine in water, 9 mmol) was added in one portion. The reaction was stirred at room temperature overnight. After removing the solvent, the oily residue was diluted with ethyl acetate and water. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and evaporated to obtain 0.42 g of 4-([4-(2-butynyloxy)phenyl]sulfonyl}-N-hydroxy-3-morpholinecarboxamide. Yield˜77.8%. mp 68-72° C. Electrospray Mass Spec 355.2(M+H)+.

後処理

  1. customrecooled to 0°
  2. stirringThe reaction was stirred at room temperature overnight
  3. customAfter removing the solvent
  4. additionthe oily residue was diluted with ethyl acetate and water
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-bca6c99a1ba34f5eb09941c198c52281
出典データセット
uspto-grants-2004_04
特許番号
US06716833B2

反応ノート

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