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4-[(2S,3R)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-1-(4-{3-[(methylsulfonyl)amino]propyl}phenyl)-4-oxoazetidin-2-yl]phenyl methyl beta-D-glucopyranosiduronate → 4-[(2S,3R)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-1-(4-{3-[(methylsulfonyl)amino]propyl}phenyl)-4-oxoazetidin-2-yl]phenyl beta-D-glucopyranosiduronic acid

HRID 600188
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HRID 600188 반응식
[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]([CH2:43][CH2:44][CH2:45][NH:46][S:47]([CH3:50])(=[O:49])=[O:48])=[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: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]([CH2:43][CH2:44][CH2:45][NH:46][S:47]([CH3:50])(=[O:49])=[O:48])=[CH:39][CH:38]=2)=[CH:17][CH:16]=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]
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참가 물질

3

반응물 1

HCID 866018744-[(2S,3R)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-1-(4-{3-[(methylsulfonyl)amino]propyl}phenyl)-4-oxoazetidin-2-yl]phenyl methyl beta-D-glucopyranosiduronate

생성물 1

HCID 670556374-[(2S,3R)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-1-(4-{3-[(methylsulfonyl)amino]propyl}phenyl)-4-oxoazetidin-2-yl]phenyl beta-D-glucopyranosiduronic acid

시약·촉매·용매 1

HCID 23434731Methanol water triethylamine용매

실험 절차

A solution of 9a in methanol/water/triethylamine (1:7:2, 1 mL) was stirred at room temperature for approximately 1 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 (9b); m/z (ES) 735 (M+Na)+, 685 (M-OH)+, 509 (M-sugar-OH)+; HRMS (ES) m/z calc'd for C34H39FN2O11S (MH+) 703.2337, found 703.2337.

후처리

  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)

출처 및 근거

ORD 기록
ord-709c13ae8ba24552a204ef4fec10ba71
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07901893B2

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