Methanol → HCID 58109697, compound

HRID 2037435Notes

Reaction equation

HRID 2037435 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N:15]2[CH2:20][CH2:19][C:18]([CH2:27][C:28]([OH:30])=[O:29])([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:17][C:16]2=[O:31])[CH:10]=1.S(Cl)(Cl)=O.[CH3:36]O>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N:15]2[CH2:20][CH2:19][C:18]([CH2:27][C:28]([O:30][CH3:36])=[O:29])([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:17][C:16]2=[O:31])[CH:10]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 25182555HCID 25182555, compound

Product 1

HCID 58109697HCID 58109697, compoundYield 23%

Procedure

A 100-mL of flask was charged with 2-(3-(2′,4′-difluorobiphenyl-3-yl)-2-oxo-6-phenyl-1,3-oxazinan-6-yl)acetic acid (1.02 g, 2.4 mmol) dissolved in MeOH (15 mL). Then thionyl chloride (418 mg, 3.5 mmol) was added dropwise slowly at 0° C. under N2 protection. The mixture was stirred overnight under reflux. The mixture was concentrated to give the crude product, which was purified by chromatography to give the pure product (230 mg, 23%).

Workup

  1. temperatureunder reflux
  2. concentrationThe mixture was concentrated
  3. customto give the crude product, which
  4. customwas purified by chromatography

Sources & evidence

ORD record
ord-90b30abf9e224012954043fba9d4cd95
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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