Triphenylphosphine → HCID 86587129, 화합물

HRID 2084932노트

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HRID 2084932 반응식
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][CH:16]([CH2:21]O)[C:17]([O:19][CH3:20])=[O:18])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH2:21][CH:16]2[C:17]([O:19][CH3:20])=[O:18])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 12016494N-[[4-(2-Butyn-1-yloxy)phenyl]sulfonyl]serine methyl ester

생성물 1

HCID 86587129HCID 86587129, 화합물수율 58%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a THF solution (10 mL) of methyl 2-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)-3-hydroxypropanoate (0.33 g, 1 mmol) and triphenylphosphine (0.32 g, 1.2 mmol), diethylazodicarboxylate (0.19 mL, 1.2 mmol) was added dropwise. The mixture was stirred at room temperature overnight. After removing the solvent, the residue was extracted with ether. The organic layer was washed with 1N NaHCO3, water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel eluting with hexane:ethyl acetate (1:1) to provide 0.18 g of 1-({[4-(2-butynyloxy)phenyl]sulfonyl}-2-aziridinecarboxylic acid, methyl ester. Yield 58.0%. Electrospray Mass Spec 310.2(M+H)+.

후처리

  1. customAfter removing the solvent
  2. extractionthe residue was extracted with ether
  3. washThe organic layer was washed with 1N NaHCO3, water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel eluting with hexane:ethyl acetate (1:1)

출처 및 근거

ORD 기록
ord-2b731932bb4b44298f172d1d059fd194
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06716833B2

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