Thionyl Chloride → HCID 118208875, compound

HRID 595254Notes

Reaction equation

HRID 595254 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C@@H:7]1[C@@H:11]([CH3:12])[O:10][C:9](=[O:13])[NH:8]1>N1C=CC=CC=1>[Cl:3][CH2:6][C@@H:7]1[C@@H:11]([CH3:12])[O:10][C:9](=[O:13])[NH:8]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 13567484HCID 13567484, compound

Product 1

HCID 118208875HCID 118208875, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Thionyl chloride (5.07 ml, 69.4 mmol) was added to a mixture of (4R,5R)-4-(hydroxymethyl)-5-methyloxazolidin-2-one (1.82 g, 13.88 mmol) in pyridine (35 mL) at 0° C. and the mixture was allowed to warm to room temperature for one hour. The mixture was then heated to 60° C. for one hour, allowed to cool to room temperature and then concentrated under reduced pressure. The crude oil was purified by column chromatography on silica to afford (4S,5R)-4-(chloromethyl)-5-methyloxazolidin-2-one. 1H NMR (500 MHz, CDCl3) δ 6.23 (s, 1H), 4.50 (qd, J=6.3, 4.6 Hz, 1H), 3.74-3.63 (m, 1H), 3.59-3.48 (m, 2H), 1.48 (d, J=6.4 Hz, 3H).

Workup

  1. temperatureThe mixture was then heated to 60° C. for one hour
  2. temperatureto cool to room temperature
  3. concentrationconcentrated under reduced pressure
  4. customThe crude oil was purified by column chromatography on silica

Sources & evidence

ORD record
ord-898e1e73b3aa42f38dc4c73667a9413a
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

Loading…