4-((2S,3R)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxo-1-{4-[(trimethylsilyl)ethynyl]phenyl}azetidin-2-yl)phenyl methyl beta-D-glucopyranosiduronate → 4-{(2S,3R)-1-(4-ethynylphenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}phenyl beta-D-glucopyranosiduronic acid

HRID 1437816ノート

反応式

HRID 1437816 の反応式
[O:1]([C:15]1[CH:20]=[CH:19][C:18]([C@@H:21]2[C@@H:24]([CH2:25][CH2:26][C@@H:27]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[OH:28])[C:23](=[O:36])[N:22]2[C:37]2[CH:42]=[CH:41][C:40]([C:43]#[C:44][Si](C)(C)C)=[CH:39][CH:38]=2)=[CH:17][CH:16]=1)[C@@H:2]1[O:10][C@H:9]([C:11]([O:13]C)=[O:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4]>CO.O.C(N(CC)CC)C>[O:1]([C:15]1[CH:16]=[CH:17][C:18]([C@@H:21]2[C@@H:24]([CH2:25][CH2:26][C@@H:27]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[OH:28])[C:23](=[O:36])[N:22]2[C:37]2[CH:38]=[CH:39][C:40]([C:43]#[CH:44])=[CH:41][CH:42]=2)=[CH:19][CH:20]=1)[C@@H:2]1[O:10][C@H:9]([C:11]([OH:13])=[O:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4]

参加物

3

反応物 1

HCID 866018734-((2S,3R)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxo-1-{4-[(trimethylsilyl)ethynyl]phenyl}azetidin-2-yl)phenyl methyl beta-D-glucopyranosiduronate

生成物 1

HCID 866018724-{(2S,3R)-1-(4-ethynylphenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}phenyl beta-D-glucopyranosiduronic acid

試薬・触媒・溶媒 1

HCID 23434731Methanol water triethylamine溶媒

実験手順

A solution of 8a in methanol/water/triethylamine (0.25 mL:1.10 mL:0.40 mL) was stirred at room temperature for approximately 6 h. The volatiles were evaporated in vacuo and the crude residue purified by preparative reversed phase high performance liquid chromatography on YMC Pack Pro C18 phase (gradient elution; 10-65% acetonitrile/water as eluent, 0.1% TFA modifier) to give the title compound (fb); m/z (ES) 574 (M−OH)+, 398; HRMS (ES) m/z calc'd for C32H31FNO9 (MH+) 592.1983, found 592.1985.

後処理

  1. customThe volatiles were evaporated in vacuo
  2. customthe crude residue purified by preparative reversed phase high performance liquid chromatography on YMC Pack Pro C18 phase (gradient elution; 10-65% acetonitrile/water as eluent, 0.1% TFA modifier)

出典と根拠

ORDレコード
ord-6f3d8b821ec64417a39759f70c840688
出典データセット
uspto-grants-2009_11
特許番号
US07622449B2

反応ノート

読み込み中…