Triethylamine → HCID 178461685, compound

HRID 473934Notes

Reaction equation

HRID 473934 reaction equation
[OH:1][C:2]([CH3:28])([CH3:27])[CH2:3][C@@:4]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1.Cl.[NH2:30][OH:31].CCN(CC)CC>CO>[OH:31][NH:30][C:17](=[NH:18])[C:16]1[CH:19]=[CH:20][C:13]([C@@H:11]([N:7]2[CH2:6][CH2:5][C@:4]([CH2:3][C:2]([OH:1])([CH3:27])[CH3:28])([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[O:9][C:8]2=[O:10])[CH3:12])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 58564188HCID 58564188, compound

Product 1

HCID 178461685HCID 178461685, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-{(S)-1-[(S)-6-(2-hydroxy-2-methyl-propyl)-2-oxo-6-phenyl-[1,3]oxazinan-3-yl]ethyl}-benzonitrile (0.50 g), hydroxylamine hydrochloride (0.18 g), and NEt3 (0.43 mL), and methanol (10 mL) was stirred at reflux temperature for 5 h. After cooling to room temperature, the solvent was evaporated, mixture was concentrated, ethyl acetate was added to the residue, and the resulting mixture was washed with water and brine. The organic solution was dried Na2SO4) and concentrated and the residue was purified by chromatography on silica gel (CH2Cl2/MeOH 98:2->93:7) to afford the title compound as a foam-like solid.

Workup

  1. temperatureat reflux temperature for 5 h
  2. customthe solvent was evaporated
  3. concentrationmixture was concentrated
  4. additionethyl acetate was added to the residue
  5. washthe resulting mixture was washed with water and brine
  6. concentrationconcentrated
  7. customthe residue was purified by chromatography on silica gel (CH2Cl2/MeOH 98:2->93:7)

Sources & evidence

ORD record
ord-6b8cfea0ec8947fb99d1a66a2ab566a6
Source dataset
uspto-grants-2014_01
Patent number
US08637505B2

Reaction notes

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