Hydroxylamine → HCID 9819974, 화합물

HRID 2084936노트

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HRID 2084936 반응식
[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]

참가 물질

8

반응물 5

HCID 787HydroxylamineHCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22644786HCID 22644786, 화합물

생성물 1

HCID 9819974HCID 9819974, 화합물수율 77.8%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-bca6c99a1ba34f5eb09941c198c52281
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06716833B2

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