Ethanolamine → HCID 10149934, compound

HRID 1991262Notes

Reaction equation

HRID 1991262 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-f2e6e50c964d4654ac7f8a8d68002fbd
Source dataset
uspto-grants-2010_01
Patent number
US07645781B2

Reaction notes

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