Sodium Carbonate → HCID 69081623, compound

HRID 2362376Notes

Reaction equation

HRID 2362376 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.C([O-])([O-])=O.[Na+].[Na+].[NH2:19][C@H:20]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Br:32])[CH:27]=1)[C@H:21]([OH:25])[C:22]([OH:24])=[O:23].O1CCOCC1>O>[Br:32][C:28]1[CH:27]=[C:26]([C@@H:20]2[C@@H:21]([C:22]([OH:24])=[O:23])[O:25][C:2](=[O:4])[NH:19]2)[CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 94429TriphosgeneHCID 69082011HCID 69082011, compound

Product 1

HCID 69081623HCID 69081623, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To triphosgene (36.5 mg, 0.123 mmol) and Na2CO3 (65.2 mg, 0.615 mmol) in Water (2.000 mL) at 0° C. was added dropwise a solution of (2S,3R)-3-amino-3-(3-bromophenyl)-2-hydroxypropanoic acid (20 mg, 0.077 mmol) in Water (0.5 mL)/1,4-Dioxane (0.5 mL). After 15 min, the ice bath was removed and stirring was continued for one hour. ethylacetate (1 ml) was added to the reaction mixture and after five minutes the ethylacetate layer was discarded and the aqueous layer was acidified to pH 2 and extracted with ethylacetate (5 mL×3). The combined organics were dried over magnesium sulfate, filtered and concentrated providing (4R,5S)-4-(3-bromophenyl)-2-oxooxazolidine-5-carboxylic acid (14.2 mg, 0.047 mmol, 61.3% yield) as a white solid. Mass spec.: 287.79 (MH)+.

Workup

  1. customthe ice bath was removed
  2. waitwas continued for one hour
  3. additionethylacetate (1 ml) was added to the reaction mixture and after five minutes the ethylacetate layer
  4. extractionextracted with ethylacetate (5 mL×3)
  5. dry with materialThe combined organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6ddb7635e5d74863b3c9045277a5c0ac
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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