HCID 86667165, compound → HCID 86667164, compound

HRID 2367938Notes

Reaction equation

HRID 2367938 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([O:11]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:9][CH2:8][CH2:7][C@@H:6]1[N:31]=[N+:32]=[N-:33])(=[O:3])[CH3:2]>CC(O)=O>[C:1]([O:4][C@H:5]1[C@H:10]([OH:11])[CH2:9][CH2:8][CH2:7][C@@H:6]1[N:31]=[N+:32]=[N-:33])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 86667165HCID 86667165, compound

Product 1

HCID 86667164HCID 86667164, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
56 °C

Procedure

Compound 3 (677 mg, 1.53 mmol) was dissolved in AcOH (10 mL), heated to 56° C. and left over night. The mixture was concentrated and purified by flash chromatography using EtOAc:n-heptan (1:1) as eluent. The reaction yielded 81% of 4. 1H-NMR (CDCl3) 4.72 (t, J=9.54 Hz, 1 H), 3.56 (m, 1 H), 3.47 (m, 1 H), 2.19 (s, 3 H), 2.00-2.10 (m, 3 H), 1.80 (m, 1 H), 1.25-1.45 (m, 3 H). HRMS calculated mass (C8H14N3O3+): 200.1030, observed mass: 200.1056.

Workup

  1. waitleft over night
  2. concentrationThe mixture was concentrated
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-88896c10c8cc4f85aabdea2be62b5cd7
Source dataset
uspto-grants-2014_04
Patent number
US08703720B2

Reaction notes

Loading…