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 600187Notes

Reaction equation

HRID 600187 reaction equation
[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]

Participants

3

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 23434731Methanol water triethylamineSolvent

Procedure

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 (8b); m/z (ES) 574 (M-OH)+, 398; HRMS (ES) m/z calc'd for C32H31FNO9 (MH+) 592.1983, found 592.1985.

Workup

  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)

Sources & evidence

ORD record
ord-d4714854f02242b3a395c0f1e1351948
Source dataset
uspto-grants-2011_03
Patent number
US07901893B2

Reaction notes

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