Triphenylphosphine → (1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethylazide

HRID 133801노트

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HRID 133801 반응식
[C:1]1([CH2:7][C@H:8]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.C1(P([N:60]=[N+:61]=[N-:62])(C2C=CC=CC=2)=O)C=CC=CC=1>O1CCCC1>[C:1]1([CH2:7][C@H:8]([N:60]=[N+:61]=[N-:62])[C:10]2[S:11][CH:12]=[CH:13][N:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 5462977Diethyl azodicarboxylateHCID 11084983(1R)-2-phenyl-1-(1,3-thiazol-2-yl)ethanol

생성물 1

HCID 10955374(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethylazide수율 82.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Following the method of Itako et al. (Irako, N.; Hamada, Y.; Shioiri, T. Tetrahedron 48(35), 1992, 7251-7264), a solution of (1R)-2-phenyl-1-(1,3-thiazol-2-yl)ethanol (1.3 g, 6.3 mmol, from Reference Example 3) in tetrahydrofuran (60 mL) is cooled to 0° C. (ice-water bath). To the solution is added successively triphenylphosphine (1.8 g, 6.9 mmol), diethylazodicarboxylate (1.1 mL, 6.9 mmol), and diphenylphosphoryl azide (DPPA, 1.6 mL, 6.9 mmol). Following the addition of reagents, the reaction mixture is allowed to warm to room temperature and stir for 47 hours. Following this period, the mixture is concentrated under reduced pressure and purified by flash chromatography (silica gel, hexanes/toluene/diethyl ether) to give 1.2 g of (1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethylazide as a pale blond oil contaminated with DPPA (detected by 1H NMR).

후처리

  1. additionthe addition of reagents
  2. waitFollowing this period
  3. concentrationthe mixture is concentrated under reduced pressure
  4. custompurified by flash chromatography (silica gel, hexanes/toluene/diethyl ether)

출처 및 근거

ORD 기록
ord-b438dc3fffec42a9adf66b796ec4c0e2
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390910B2

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