Sodium Cyanide → HCID 67055600, compound

HRID 600192Notes

Reaction equation

HRID 600192 reaction equation
C([O:4][C@@H:5]1[C@@H:49]([O:50]C(=O)C)[C@H:48]([O:54]C(=O)C)[C@@H:47]([C:58]([O:60]C)=[O:59])[O:46][C@H:6]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]2[C@@H:17]([CH2:18][CH2:19][C@H:20]([O:28]C(=O)C)[C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[C:16](=[O:32])[N:15]2[C:33]2[CH:38]=[CH:37][C:36]([C:39]#[C:40][C:41]([NH:43][CH2:44][CH3:45])=[O:42])=[CH:35][CH:34]=2)=[CH:10][CH:9]=1)(=O)C.[C-]#N.[Na+]>CO>[O:7]([C:8]1[CH:9]=[CH:10][C:11]([C@@H:14]2[C@@H:17]([CH2:18][CH2:19][C@@H:20]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[OH:28])[C:16](=[O:32])[N:15]2[C:33]2[CH:34]=[CH:35][C:36]([C:39]#[C:40][C:41]([NH:43][CH2:44][CH3:45])=[O:42])=[CH:37][CH:38]=2)=[CH:12][CH:13]=1)[C@@H:6]1[O:46][C@H:47]([C:58]([OH:60])=[O:59])[C@@H:48]([OH:54])[C@H:49]([OH:50])[C@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 866018784-((2S,3R)-3-[(3S)-3-(acetyloxy)-3-(4-fluorophenyl)propyl)-1-{4-(3-(ethylamino)-3-oxoprop-1-yn-1-yl]phenyl}-4-oxoazetidin-2-yl)phenyl methyl 2,3,4-tri-O-acetyl-beta-D-glucopyranosiduronate

Product 1

HCID 67055600HCID 67055600, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-((2S,3R)-3-[(3S)-3-(acetyloxy)-3-(4-fluorophenyl)propyl]-1-{4-(3-(ethylamino)-3-oxoprop-1-yn-1-yl]phenyl}-4-oxoazetidin-2-yl)phenyl methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate (11a) (22.0 mg, 0.026 mmol) and sodium cyanide (˜1 mg, 0.020 mmol) in methanol (3 mL) was heated to 45° C. After 18 h, the reaction mixture was concentrated under reduced pressure and dissolved in methanol/water/triethylamine (1:3:1, 2.5 mL). After stirring 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; 10-60% acetonitrile/water as eluent, 0.1% TFA modifier) to give the title compound (11b) m/z (ES) 663.0 (M+H)+; HRMS (ES) m/z calcd. for C35H36FN2O10 (MH+) 663.2354, found 663.2341.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutiondissolved in methanol/water/triethylamine (1:3:1, 2.5 mL)
  3. customthe volatiles were evaporated in vacuo
  4. customthe crude residue purified by preparative reversed phase high performance liquid chromatography on YMC Pack Pro C18 phase (gradient elution; 10-60% acetonitrile/water as eluent, 0.1% TFA modifier)

Sources & evidence

ORD record
ord-2480cea1bd3849cbb5b256970017c2bc
Source dataset
uspto-grants-2011_03
Patent number
US07901893B2

Reaction notes

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