HCID 118511758, compound → HCID 89810638, compound

HRID 1399983Notes

Reaction equation

HRID 1399983 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([C@@H:8]([O:10]C(=O)[C@H](NC(OC(C)(C)C)=O)C(C)C)[CH3:9])=[N:6][CH:7]=1>CO>[Br:1][C:2]1[CH:3]=[N:4][C:5]([CH:8]([OH:10])[CH3:9])=[N:6][CH:7]=1

Participants

3

Reactant 1

HCID 118511758HCID 118511758, compound

Product 1

HCID 89810638HCID 89810638, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Amberlite® basic ion exchange resin and ii (15.4 g, 38.3 mmol) were stirred in MeOH (50 mL) overnight at RT. The suspension was filtered through a pad of silica using 1:1 MeOH/DCM and the filtrate concentrated in vacuo. Crystallisation from hot heptane gave Precursor 82 (5.85 g). (1S)-1-(5-bromopyrimidin-2-yl)ethanol (Precursor 83) was similarly prepared using Boc-L-valine. Mitsunobu inversion of one enantiomer to the desired enantiomer may also be employed.

Workup

  1. filtrationThe suspension was filtered through a pad of silica using 1:1 MeOH/DCM
  2. concentrationthe filtrate concentrated in vacuo
  3. customCrystallisation from hot heptane

Sources & evidence

ORD record
ord-f258446119374115a3b532ada07d8479
Source dataset
uspto-grants-2014_12
Patent number
US08906902B2

Reaction notes

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