Water → HCID 71542528, compound

HRID 2199769Notes

Reaction equation

HRID 2199769 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:21]2[CH2:25][C@H:24]([CH2:26][OH:27])[O:23][C:22]2=[O:28])[CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[N:10][C:11]([NH:14][C:15]2[N:19]([CH3:20])[N:18]=[N:17][N:16]=2)=[CH:12][CH:13]=1.C(N(CC)CC)C.[P:36](Cl)(Cl)(Cl)=[O:37].[OH2:41].C1C[O:45]CC1>>[P:36]([OH:37])([OH:45])([O:27][CH2:26][C@@H:24]1[O:23][C:22](=[O:28])[N:21]([C:4]2[CH:5]=[CH:6][C:7]([C:8]3[CH:9]=[N:10][C:11]([NH:14][C:15]4[N:19]([CH3:20])[N:18]=[N:17][N:16]=4)=[CH:12][CH:13]=3)=[C:2]([F:1])[CH:3]=2)[CH2:25]1)=[O:41]

Participants

6

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 71542526HCID 71542526, compound

Product 1

HCID 71542528HCID 71542528, compoundYield 57%

Procedure

(R)-3-(3-fluoro-4-(6-((1-methyl-1H-tetrazol-5-yl)amino)pyridin-3-yl)phenyl)-5-(hydroxylmethyl)oxazolidin-2-one (200 mg, 0.52 mmol) was dissolved in 30 mL THF, and triethylamine (262 mg, 2.6 mmol) was added under ice-water bath. After half an hour, phosphorus oxychloride (397 mg, 2.6 mmol) was added, and reacted at room temperature for 12 h. Water (180 mg, 10 mmol) was added dropwise. After filtration, 140 mg of product was obtained, at a yield of 57%.

Workup

  1. waitAfter half an hour
  2. customreacted at room temperature for 12 h
  3. filtrationAfter filtration

Sources & evidence

ORD record
ord-de09d4e7d84c4798a66515902764d119
Source dataset
uspto-grants-2016_06
Patent number
US09359344B2

Reaction notes

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