Triphenylphosphine → 2-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenoxy)-propionic Acid Ethyl Ester

HRID 11619

반응식

HRID 11619 반응식
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][CH2:7][C:8]([N:10]2[CH2:15][C@H:14]([CH3:16])[N:13]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:12][C@H:11]2[CH3:25])=[O:9])=[C:4]([OH:28])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:48]([O:50][C:51](=[O:55])[C@@H:52](O)[CH3:53])[CH3:49].C(OC(N=NC(OCC)=O)=O)C>O1CCCC1>[CH2:48]([O:50][C:51](=[O:55])[CH:52]([O:28][C:4]1[CH:3]=[C:2]([Cl:1])[CH:27]=[CH:26][C:5]=1[O:6][CH2:7][C:8]([N:10]1[CH2:15][C@H:14]([CH3:16])[N:13]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:12][C@H:11]1[CH3:25])=[O:9])[CH3:53])[CH3:49]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 92831(L)-ethyl lactateHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 537887242-(4-Chloro-2-hydroxy-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone

생성물 1

HCID 696555862-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenoxy)-propionic Acid Ethyl Ester수율 85.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-(4-chloro-2-hydroxy-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.076 g, 0.18 mmol), triphenylphosphine (0.076 g, 0.29 mmol) and (2S)-2-hydroxy-propionic acid ethyl ester (0.036 g, 0.31 mmol) in tetrahydrofuran (1 mL) was added diethyl-azodicarboxylate (0.049 g, 0.29 mmol). The resulting mixture was stirred at ambient temperature overnight. The reaction was concentrated in-vacuo. Chromatography on silica gel gave the title compound (0.078 g)

후처리

  1. concentrationThe reaction was concentrated in-vacuo

출처 및 근거

ORD 기록
ord-9b2b8380db7e41eda5472024bba50d5f
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098212B2

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