Triphenylphosphine → HCID 66643884, 화합물

HRID 1695327노트

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HRID 1695327 반응식
[CH3:1][O:2][C:3]([C:5]1[NH:6][N:7]=[C:8]([OH:10])[CH:9]=1)=[O:4].[CH3:11][C:12]1[O:16][N:15]=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13]=1[CH2:23]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[NH:6][N:7]=[C:8]([O:10][CH2:23][C:13]2[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:15][O:16][C:12]=2[CH3:11])[CH:9]=1)=[O:4]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2776149(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanolHCID 1784986025-Hydroxy-1H-pyrazole-3-carboxylic acid methyl ester

생성물 1

HCID 66643884HCID 66643884, 화합물수율 27.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 5-hydroxy-2H-pyrazole-3-carboxylic acid methyl ester (1.30 g, 9.15 mmol) and (5-methyl-3-phenyl-isoxazol-4-yl)-methanol (1.73 g, 9.15 mmol) in THF (80 mL) at 5° C. under argon was added triphenylphosphine (3.12 g, 11.9 mmol), then diethyl azodicarboxylate (2.07 g, 11.9 mmol) was added dropwise. The reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was then evaporated. Purification by chromatography (silica, heptane:ethyl acetate=1:1 then dichloromethane:methanol=9:1) gave a colorless oil (800 mg) which was triturated with diisopropylether and further purified using a 5×50 cm Chiralpak AD column at room temperature using an isopropanol:heptane (2:8) mobile phase with UV detection at 220 nM to afford the title compound (250 mg, 9%) as a white solid. MS: m/e=328.3 [M+H]+.

후처리

  1. customThe reaction mixture was then evaporated
  2. customPurification by chromatography (silica, heptane

출처 및 근거

ORD 기록
ord-27ba284d6b304aacbbd8eb4a79295903
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163728B2

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