Ammonia → HCID 10286236, compound

HRID 896121Notes

Reaction equation

HRID 896121 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([N:11]3[CH2:15][C@H:14]([C:16](OCCCC)=[O:17])[O:13][C:12]3=[O:23])=[CH:10][C:5]=2[S:4][C:3]1=[O:24].[NH3:25]>CO.O1CCCC1>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([N:11]3[CH2:15][C@H:14]([C:16]([NH2:25])=[O:17])[O:13][C:12]3=[O:23])=[CH:10][C:5]=2[S:4][C:3]1=[O:24]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 68489799HCID 68489799, compound

Product 1

HCID 10286236HCID 10286236, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

The butyl (5R)-3-(2,3-dihydro-3-methyl-2-oxo-6-benzothiazolyl)-2-oxo-5-oxazolidinecarboxylate (Step 2, 685 mg, 1.95 mmol) is treated with 7N ammonia in MeOH (19 mL) with vigorous stirring, and the mixture is diluted with additional MeOH (20 mL) and tetrahydrofuran (20 mL) and stirred at ambient temperature for 1 h. The resulting slurry is concentrated under reduced pressure and then triturated and filtered from acetone to give the title compound, mp 274-276° C. (dec.); MS (ESI−) for C12H11N3O4S m/z 292 (M−H)−; [α]25D−27 (c 0.98, DMSO).

Workup

  1. concentrationThe resulting slurry is concentrated under reduced pressure
  2. customtriturated
  3. filtrationfiltered from acetone

Sources & evidence

ORD record
ord-0f2216e1e8e04016aa6c3db2c94b152a
Source dataset
uspto-grants-2005_07
Patent number
US06919329B2

Reaction notes

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