Methylamine → HCID 10286376, compound

HRID 723849Notes

Reaction equation

HRID 723849 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-8e7ccaf824fb420b953e5afaa7424847
Source dataset
uspto-grants-2006_11
Patent number
US07141588B2

Reaction notes

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