Triethylamine → 6-Methyl-6-phenyl-3-(4-phenylthiazol-2-yl)-1,3-oxazinan-2-one

HRID 2037440Notes

Reaction equation

HRID 2037440 reaction equation
[C:1]1([C:7]([OH:23])([CH2:9][CH2:10][NH:11][C:12]2[S:13][CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:16]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC.Cl[C:32](Cl)([O:34]C(=O)OC(Cl)(Cl)Cl)Cl>>[CH3:8][C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[O:23][C:32](=[O:34])[N:11]([C:12]2[S:13][CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:16]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 581096672-Phenyl-4-(4-phenylthiazol-2-ylamino)butan-2-ol

Product 1

HCID 581091276-Methyl-6-phenyl-3-(4-phenylthiazol-2-yl)-1,3-oxazinan-2-oneYield 114.1%

Procedure

To a solution of 2-phenyl-4-(4-phenylthiazol-2-ylamino)butan-2-ol (50 mg, 0.15 mmol) and Et3N (80 mg, 0.75 mmol) in CH2CH2 (5 mL) was added triphosgene (15 mg, 0.05 mmol) at 0° C. Then, the mixture was stirred at rt overnight. The reaction solution was concentrated to give an oil, which was purified by column chromatography (1:2 petroleum ether/EtOAc) to afford 6-methyl-6-phenyl-3-(4-phenylthiazol-2-yl)-1,3-oxazinan-2-one (20 mg, 37%). LC-MS Method 3, tR=1.446 min, m/z=351. 1H NMR (CDCl3, 400 Hz): 1.80 (s, 3H), 2.45 (m, 1H), 2.65 b (m, 1H), 3.70 (m, 1H), 4.42 (m, 1H), 7.18 (s, 1H), 7.20-7.40 (m, 8H), 7.80 (d, 2H).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customto give an oil, which
  3. customwas purified by column chromatography (1:2 petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-41ab462b6d1e45408da14a7b3065e6f1
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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