Ammonia → HCID 10236567, compound

HRID 1991259Notes

Reaction equation

HRID 1991259 reaction equation
[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([N:12]3[CH2:16][C@H:15]([C:17](OCCCC)=[O:18])[O:14][C:13]3=[O:24])=[CH:11][C:6]=2[S:5][C:4]1=[O:25])[CH3:2].[NH3:26]>CO>[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([N:12]3[CH2:16][C@H:15]([C:17]([NH2:26])=[O:18])[O:14][C:13]3=[O:24])=[CH:11][C:6]=2[S:5][C:4]1=[O:25])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 68490558HCID 68490558, compound

Product 1

HCID 10236567HCID 10236567, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The butyl(5R)-3-(2,3-dihydro-3-ethyl-2-oxo-6-benzothiazolyl)-2-oxo-5-oxazolidinecarboxylate (Step 3, 500 mg, 1.37 mmol) is treated with 7N ammonia in MeOH (14 mL) with vigorous stirring, and the mixture is diluted with additional MeOH (20 mL) and stirred at ambient temperature for 30 mins. The resulting slurry is filtered to give the title compound, mp 211-212.5° C.; MS (ESI+) for C13H13N3O4S m/z 308 (M+H)+; [α]25D−25 (c 0.92, DMSO).

Workup

  1. filtrationThe resulting slurry is filtered

Sources & evidence

ORD record
ord-e122d8e3c4f44ea0a180f850bd810bac
Source dataset
uspto-grants-2010_01
Patent number
US07645781B2

Reaction notes

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