Triethylamine → HCID 86659550, compound

HRID 455906Notes

Reaction equation

HRID 455906 reaction equation
[C:1]([NH:8][O:9][CH2:10][CH2:11][OH:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Br:13][C:14]([CH3:19])([CH3:18])[C:15](O)=[O:16].C(N(CC)CC)C>ClCCl>[Br:13][C:14]([CH3:19])([CH3:18])[C:15]([O:12][CH2:11][CH2:10][O:9][NH:8][C:1]([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 749242-Bromo-2-methylpropanoic acidHCID 45092372HCID 45092372, compound

Product 1

HCID 86659550HCID 86659550, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-Boc-2-(aminooxy)ethanol (14.5 g, 81.8 mmol) and the NHS ester of 2-bromoisobutyric acid (22.2 g, 84 mmol) in anhydrous dichloromethane (300 mL) was cooled in an ice bath. Anhydrous triethylamine (11.5 mL, 83 mmol, 1.01 eq.) and N,N-dimethylaminopyridine (1 g, 8.2 mmol, 10 mol %) were added. The ice bath was removed and the reaction was allowed to warm to room temperature and stirring was continued for 18 h. The reaction mixture was concentrated to dryness under reduced pressure giving a viscous oil, which was loaded onto a silica gel column (about 200 g SiO2). Gradient elution (100% hexanes→15% ethyl acetate in hexanes) afforded the product as a pale, clear oil (20.8 g, 78%). (Rf=0.74, ethyl acetate:hexanes (1:2)). 1H NMR (CDCl3, 300 MHz): δ 7.42 (s, 1H), 4.40 (apparent t, J=3.0 Hz, 2H), 4.05 (apparent t, J=3.0 Hz, 2H), 1.92 (s, 6H), 1.45 (s, 9H). 13C NMR (CDCl3, 300 MHz): δ 172.2, 156.9, 82.1, 74.0, 63.3, 55.8, 31.0, 28.4. EIMS m/z: 348, ([M+Na]+), 350 ([M+Na]+).

Workup

  1. customThe ice bath was removed
  2. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  3. customgiving a viscous oil, which
  4. washGradient elution (100% hexanes→15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-031a9ef626bb4c4a9d5730531c629989
Source dataset
uspto-grants-2013_07
Patent number
US08497356B2

Reaction notes

Loading…