Methylamine → HCID 10286376, compound

HRID 896125Notes

Reaction equation

HRID 896125 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]([O:18]CCCC)=O)[O:13][C:12]3=[O:23])=[CH:10][C:5]=2[S:4][C:3]1=[O:24].[CH3:25][NH2:26]>CO>[CH3:25][NH:26][C:16]([C@@H:14]1[O:13][C:12](=[O:23])[N:11]([C:9]2[CH:8]=[CH:7][C:6]3[N:2]([CH3:1])[C:3](=[O:24])[S:4][C:5]=3[CH:10]=2)[CH2:15]1)=[O:18]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 68489799HCID 68489799, compound

Product 1

HCID 10286376HCID 10286376, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The butyl (5R)-3-(2,3-dihydro-3-methyl-2-oxo-6-benzothiazolyl)-2-oxo-5-oxazolidinecarboxylate (EXAMPLE 29, Step 2, 300 mg, 0.856 mmol) is treated with 2N methylamine in MeOH (8.6 mL) with vigorous stirring, and the mixture is diluted with additional MeOH (10 mL) and stirred at ambient temperature for 1 h. The resulting slurry is filtered to give the title compound, mp 264-267° C.; MS (ESI+) for C13H13N3O4S m/z 308 (M+H)+; [α]25D−44 (c 0.92, DMSO).

Workup

  1. filtrationThe resulting slurry is filtered

Sources & evidence

ORD record
ord-b3f8540d9f5b417b81d092c9b78fcc82
Source dataset
uspto-grants-2005_07
Patent number
US06919329B2

Reaction notes

Loading…