Hydrochloric Acid → HCID 131731129, compound

HRID 2274991Notes

Reaction equation

HRID 2274991 reaction equation
[ClH:1].[NH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[I:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Br)=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C.O>[ClH:1].[I:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 9542584-Iodobenzyl bromideHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 131731129HCID 131731129, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of ethyl glycinate hydrochloride (944 mg) in DMF (6.0 mL) was stirred for 5 min. p-Iodobenzyl bromide (2.00 g) was added. The heterogeneous system was warmed to 50° C. and stirred for 5 min, during which time, most solids dissolved. K2CO3 (2.80 g, granular) was added steadily over 5 min. After 2 h, the reaction was cooled to 23° C. Conc. aq. HCl (3.3 mL) was added, followed by H2O (7.0 mL). The heterogeneous mix was stirred for 15 min and filtered (the cake was washed with CH3CN (4×5 mL)). The net filtrate was concentrated until no CH3CN remained. The crude product solution was filtered through a 0.45 micron Teflon filter and loaded directly onto a Teledyne Isco ‘gold’ 100 gram column and flashed (Eluent: 0.05% w/v aq. HCl/CH3CN 95:5→0:100), giving DK (688 mg, 29% yield) as an HCl salt. 1H NMR (DMSO-d6, 300 MHz): δ (ppm) 9.78 (s, 2H), 7.84 (d, J=7.8 Hz, 2H), 7.36 (d, J=7.8 Hz, 2H), 4.23 (q, J=7.0 Hz, 2H), 4.15 (s, 2H), 3.95 (s, 2H), 1.25 (t, J=7.0 Hz, 3H). LCMS-ESI+: calc'd for C11H15INO2: 320.0 (M+H+). Found: 319.9 (M+H+).

Workup

  1. additionwas added
  2. dissolutiondissolved
  3. waitAfter 2 h
  4. temperaturethe reaction was cooled to 23° C
  5. additionThe heterogeneous mix
  6. stirringwas stirred for 15 min
  7. filtrationfiltered (the cake
  8. washwas washed with CH3CN (4×5 mL))
  9. concentrationThe net filtrate was concentrated until no CH3CN
  10. filtrationThe crude product solution was filtered through a 0.45 micron Teflon
  11. filtrationfilter

Sources & evidence

ORD record
ord-0ef7c80002ac47f9ab4754f224fce737
Source dataset
uspto-grants-2015_09
Patent number
US09127006B2

Reaction notes

Loading…