Sodium Cyanide → HCID 67055604, compound

HRID 600191Notes

Reaction equation

HRID 600191 reaction equation
C([O:4][C@@H:5]1[C@@H:47]([O:48]C(=O)C)[C@H:46]([O:52]C(=O)C)[C@@H:45]([C:56]([O:58]C)=[O:57])[O:44][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]([OH:43])=[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]([OH:43])=[O:42])=[CH:37][CH:38]=2)=[CH:12][CH:13]=1)[C@@H:6]1[O:44][C@H:45]([C:56]([OH:58])=[O:57])[C@@H:46]([OH:52])[C@H:47]([OH:48])[C@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 86601877HCID 86601877, compound

Product 1

HCID 67055604HCID 67055604, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-{(2S,3R)-3-[(3S)-3-(acetyloxy)-3-(4-fluorophenyl)propyl]-1-[4-(carboxyethynyl)phenyl]-4-oxoazetidin-2-yl}phenyl methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate (10d) and sodium cyanide (˜1 mg, 0.020 mmol) in methanol (3 mL) was heated to 45° C. After 22 h, the reaction mixture was concentrated under reduced pressure and dissolved in methanol/water/triethylamine (1:7:2, 1 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 (10e), m/z (ES) 442.0 (M-sugar-OH)+, 618.0 (M-OH)+; HRMS (ES) m/z calcd. for C33H31FNO11 (MH+) 636.1881, found 636.1889

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutiondissolved in methanol/water/triethylamine (1:7:2, 1 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-dcbbdbabf497421987d7b12f6c8ebe0c
Source dataset
uspto-grants-2011_03
Patent number
US07901893B2

Reaction notes

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