Thionyl Chloride → HCID 86673422, compound

HRID 2362378Notes

Reaction equation

HRID 2362378 reaction equation
[O:1]=[C:2]1[NH:6][C@H:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]#[C:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:8]=2)[C@@H:4]([C:21]([OH:23])=O)[O:3]1.S(Cl)([Cl:26])=O>ClCCl>[O:1]=[C:2]1[NH:6][C@H:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]#[C:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:8]=2)[C@@H:4]([C:21]([Cl:26])=[O:23])[O:3]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 69084254HCID 69084254, compound

Product 1

HCID 86673422HCID 86673422, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4R,5S)-2-oxo-4-(3-(phenylethynyl)phenyl)oxazolidine-5-carboxylic acid (120 mg, 0.390 mmol) in dichloromethane (5 mL) was added thionyl chloride (0.285 mL, 3.90 mmol) and the solution was heated to reflux for 3 h. The reaction mixture was concentrated in vacuo providing (4R,5S)-2-oxo-4-(3-(phenylethynyl)phenyl)oxazolidine-5-carbonyl chloride (127 mg, 0.370 mmol, 95% yield) as a light brown wax.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 3 h
  3. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-587dca2e93324adaa6bb10edcec02890
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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