Ammonia → HCID 10286236, compound

HRID 1991257Notes

Reaction equation

HRID 1991257 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-a2c06f398fe74d19845780ec4d0693a6
Source dataset
uspto-grants-2010_01
Patent number
US07645781B2

Reaction notes

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