Triethylamine → HCID 59437186, compound

HRID 75149Notes

Reaction equation

HRID 75149 reaction equation
[C:1]12([CH2:11][NH:12][CH2:13][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)[OH:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.CCN(CC)CC.Cl[C:31](Cl)([O:33]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[C:1]12([CH2:11][N:12]3[CH2:13][CH:14]([C:16]4[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=4)[O:15][C:31]3=[O:33])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 59437178HCID 59437178, compound

Product 1

HCID 59437186HCID 59437186, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

4-(2-((1-adamantylmethyl)amino)-1-hydroxyethyl)phenol (50 mg, 0.166 mmol) and Et3N (34 mg, 0.33 mmol) were dissolved in dry CH2Cl2 (1 mL) and the solution was cooled to 0° C. Triphosgene (19.7 mg, 0.066 mmol) in dry CH2Cl2 (1 mL) was added dropwise slowly. The mixture was allowed to warm to rt and stirred overnight. The solution was concentrated to give a residue, which was purified by preparative HPLC to afford 3-adamantan-1-ylmethyl-5-(4-hydroxy-phenyl)-oxazolidin-2-one (2.40 mg, 4.4%). 1H NMR: (CDCl3, 400 MHz): δ=1.54 (s, 6H), 1.58-1.65 (d, 3H), 1.66-1.75 (d, 3H), 1.99 (s, 3H), 2.80-2.87 (d, 1H), 3.02-3.08 (d, 1H), 3.50-3.56 (t, 1H), 3.93-4.00 (t, 1H), 5.40-5.48 (t, 1H), 6.82-6.90 (d, 1H), 7.20-7.26 (d, 1H); MS m/z=328

Workup

  1. temperatureto warm to rt
  2. concentrationThe solution was concentrated
  3. customto give a residue, which
  4. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-10bbda72ebe64dd48f0845fc5a07d984
Source dataset
uspto-grants-2014_09
Patent number
US08835426B2

Reaction notes

Loading…