Ethanolamine → HCID 10149934, compound

HRID 896126Notes

Reaction equation

HRID 896126 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].[CH2:25]([CH2:27][NH2:28])[OH:26]>C(#N)C>[OH:26][CH2:25][CH2:27][NH:28][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 700EthanolamineHCID 68489799HCID 68489799, compound

Product 1

HCID 10149934HCID 10149934, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 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) in acetonitrile (3.4 mL) is treated with ethanolamine (103 μL, 1.71 mmol) and stirred at ambient temperature for 18 h. Solvent is removed under reduced pressure, and the crude product is triturated and filtered from hot ethyl acetate to give the title compound, mp 217-219° C.; MS (ESI+) for C14H15N3O5S m/z 338 (M+H)+; [α]25D−43 (c 0.99, DMSO).

Workup

  1. customSolvent is removed under reduced pressure
  2. customthe crude product is triturated
  3. filtrationfiltered from hot ethyl acetate

Sources & evidence

ORD record
ord-e84e25f00f894bb6aa4f50367f4df548
Source dataset
uspto-grants-2005_07
Patent number
US06919329B2

Reaction notes

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