Triphenylphosphine → 3-[2-(t-Butoxycarbonylamino)ethoxy]isoxazole

HRID 1064344노트

반응식

HRID 1064344 반응식
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[C:15]([O:19][C:20]([NH:22][CH2:23][CH2:24][OH:25])=[O:21])([CH3:18])([CH3:17])[CH3:16].O[C:27]1[CH:31]=[CH:30][O:29][N:28]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:15]([O:19][C:20]([NH:22][CH2:23][CH2:24][O:25][C:27]1[CH:31]=[CH:30][O:29][N:28]=1)=[O:21])([CH3:18])([CH3:17])[CH3:16]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 178516613HCID 178516613, 화합물

생성물 1

HCID 222735143-[2-(t-Butoxycarbonylamino)ethoxy]isoxazole수율 44.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Diisopropyl azodicarboxylate (1.1 ml, 5.5 mmol) was added dropwise to a solution of 2-(t-butoxycarbonylamino)ethanol (850 μl, 5.5 mmol), 3-hydroxyisoxazole (Method 75; 425 mg, 5 mmol) and triphenylphosphine (1.44 g, 5.5 mmol) in THF (20 ml) and the mixture was stirred at ambient temperature for 18 hours. The solvent was evaporated and the residue purified by flash chromatography on silica gel eluting with iso-hexane:EtOAc (100:0 increasing in polarity to 4:1) to give the title compound (506 mg, 44%) as a white solid. NMR 1.43 (s, 9H), 3.56 (m, 2H), 4.32 (m, 2H), 4.90 (s, 1H), 5.98 (s, 1H), 8.16 (s, 1H); m/z 229.

후처리

  1. customThe solvent was evaporated
  2. customthe residue purified by flash chromatography on silica gel eluting with iso-hexane:EtOAc (100:0 increasing in polarity to 4:1)

출처 및 근거

ORD 기록
ord-c634e0685a3a4003aadbc5d94019f189
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06969714B2

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