Hydrogen Bromide → HCID 20446777, compound

HRID 2417889Notes

Reaction equation

HRID 2417889 reaction equation
[BrH:1].[OH:2][C:3]1[CH:4]=[C:5]([CH:10]([OH:28])[CH2:11][NH:12][C:13]([CH3:27])([CH3:26])[CH2:14][NH:15][C:16](=[O:25])[CH2:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:7][C:8]=1[OH:9].[C:29](Cl)(=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31].Br>FC(F)(F)C(O)=O>[BrH:1].[C:29]([O:28][CH:10]([C:5]1[CH:6]=[CH:7][C:8]([O:9][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[C:3]([O:2][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[CH:4]=1)[CH2:11][NH:12][C:13]([CH3:26])([CH3:27])[CH2:14][NH:15][C:16](=[O:25])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 62493Pivaloyl chlorideHCID 70514274HCID 70514274, compound

Product 1

HCID 20446777HCID 20446777, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1-(3,4-dihydroxyphenyl)-2-[1,1-dimethyl-2-(2-phenoxyacetamido)ethylamino]ethanol hydrobromide (0.8 g.) in trifluoroacetic acid (5.4 ml.) was treated with pivaloyl chloride (1.12 ml.) and the mixture was heated under reflux for 40 minutes. The mixture was then evaporated and the residue was dissolved in ether. The solution obtained was treated with ethereal hydrogen bromide until just acid, where upon an oily solid separated. Trituration of this material with ether (20 ml.) gave the triester, 1-[3,4-bis(pivaloyloxy)phenyl]-2-[1,1-dimethyl-2-(2-phenoxyacetamido)ethylamino]ethyl pivaloate hydrobromide, as a solid (0.6 g.) m.p. 106°-110° C., NMR δ: 8.8 (2H, broad singlet, N+H2); 8.45 (1H, triplet, NHCO); 7.8-6.8 (8H, complex, aromatic protons); 5.43 (1H, broad, =CHO); 3.58 (2H, singlet, CHHD 2OPh); 4.0-3.0 (complex, CH2NH); 1.3-1.2 (33H, broad singlet, C.CH3).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 40 minutes
  3. customThe mixture was then evaporated
  4. dissolutionthe residue was dissolved in ether
  5. customThe solution obtained
  6. customseparated

Sources & evidence

ORD record
ord-69342ab7e76c4473bd4331b8a8c1ea1d
Source dataset
uspto-grants-1984_09
Patent number
US04470997

Reaction notes

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