Methylamine → HCID 10286505, compound

HRID 723852Notes

Reaction equation

HRID 723852 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]([O:19]CCCC)=O)[O:14][C:13]3=[O:24])=[CH:11][C:6]=2[S:5][C:4]1=[O:25])[CH3:2].[CH3:26][NH2:27]>CO.CCOCC>[CH3:26][NH:27][C:17]([C@@H:15]1[O:14][C:13](=[O:24])[N:12]([C:10]2[CH:9]=[CH:8][C:7]3[N:3]([CH2:1][CH3:2])[C:4](=[O:25])[S:5][C:6]=3[CH:11]=2)[CH2:16]1)=[O:19]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 68490558HCID 68490558, compound

Product 1

HCID 10286505HCID 10286505, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

The butyl (5R)-3-(2,3-dihydro-3-ethyl-2-oxo-6-benzothiazolyl)-2-oxo-5-oxazolidinecarboxylate (EXAMPLE 30, Step 3, 300 mg, 0.823 mmol) is treated with 2N methylamine in MeOH (8.2 mL), and the mixture is stirred at ambient temperature for 1 h. The resulting slurry is diluted with Et2O (10 mL) and filtered to give the title compound, mp 227–229° C.; MS (ESI+) for C14H15N3O4S m/z 322 (M+H)+; [α]25D−43 (c 0.93, DMSO).

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-73404eaed6394e0686ca7de88f46abd2
Source dataset
uspto-grants-2006_11
Patent number
US07141588B2

Reaction notes

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