m-Tolyl isocyanate → HCID 44231031, compound

HRID 1907259Notes

Reaction equation

HRID 1907259 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][C@@H:14]([OH:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=O)=O)=CC=1.[N:22]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[CH:26]=1)=[C:23]=[O:24].C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[C:15]1([C@@H:14]2[O:21][C:23](=[O:24])[N:22]([C:25]3[CH:26]=[C:27]([CH3:31])[CH:28]=[CH:29][CH:30]=3)[CH2:12][CH2:13]2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 69303m-Tolyl isocyanateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 12511151HCID 12511151, compound

Product 1

HCID 44231031HCID 44231031, compoundYield 6.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-3-hydroxy-3-phenylpropyl 4-methylbenzenesulfonate (100 mg, 0.327 mmol) and 1-isocyanato-3-methylbenzene (44 mg, 0.327 mmol) in CH2Cl2 (2 mL) was added DBU (149 mg, 0.981 mmol) and the reaction mixture was refluxed overnight. After the solvent was removed under reduced pressure, the residue was separated by preparative HPLC to give (R)-6-phenyl-3-m-tolyl-1,3-oxazinan-2-one (5.34 mg, 6%:). LC-MS (10-80) tR=2.439 min, m/z=268; 1H NMR (CDCl3): 2.30-2.34 (m, 5H), 3.63-3.68 (m, 1H), 3.80-3.86 (m, 1H), 5.49 (dd, 1H), 7.09-7.45 (m, 9H).

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. customAfter the solvent was removed under reduced pressure
  3. customthe residue was separated by preparative HPLC

Sources & evidence

ORD record
ord-3cc3d7d415f54fee813f3518f04c8339
Source dataset
uspto-grants-2013_12
Patent number
US08598160B2

Reaction notes

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