Ammonium Hydroxide → HCID 69083790, compound

HRID 2362379Notes

Reaction equation

HRID 2362379 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](Cl)=[O:22])[O:3]1.[OH-].[NH4+:25]>O1CCCC1>[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]([NH2:25])=[O:22])[O:3]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 86673422HCID 86673422, compound

Product 1

HCID 69083790HCID 69083790, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To (4R,5S)-2-oxo-4-(3-(phenylethynyl)phenyl)oxazolidine-5-carbonyl chloride (120 mg, 0.368 mmol) in tetrahydrofuran (1 mL) was added ammonium hydroxide (3 mL, 23.11 mmol) dropwise. One hour later, the reaction mixture was extracted with ethylacetate (10 mL×3) and the combined organic layer was dried over magnesium sulfate, filtered, and concentrated to obtain (4R,5S)-2-oxo-4-(3-(phenylethynyl)phenyl)oxazolidine-5-carboxamide (114 mg, 0.354 mmol, 96% yield) as a white solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 4.66 (d, J=5.49 Hz, 1H) 4.88 (d, J=5.49 Hz, 1H) 7.37-7.68 (m, 11H) 7.79 (s, 1H). Mass spec.: 307.1 (MH)+.

Workup

  1. extractionOne hour later, the reaction mixture was extracted with ethylacetate (10 mL×3)
  2. dry with materialthe combined organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2fafc50bcfa34d199c633c010ce1405b
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

Loading…