Lithium hydroxide, monohydrate → HCID 178461797, compound

HRID 968230Notes

Reaction equation

HRID 968230 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][S:9][C:10]1[N:18]=[C:17]2[C:13]([N:14]=[C:15]([NH:19]C(=O)OCC)[NH:16]2)=[C:12]([NH:25][C@H:26]([CH3:29])[CH2:27][OH:28])[N:11]=1.O.[OH-].[Li+]>O1CCOCC1.O>[NH3:11].[NH2:19][C:15]1[NH:16][C:17]2[C:13]([N:14]=1)=[C:12]([NH:25][C@H:26]([CH3:29])[CH2:27][OH:28])[N:11]=[C:10]([S:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])[N:18]=2

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 178473460HCID 178473460, compound

Product 2

HCID 222AmmoniaHCID 178461797HCID 178461797, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of the product from example 4, step (f) (0.042 g) and lithium hydroxide monohydrate (16 mg) in dioxan (4 ml) and water (2 ml) was heated under reflux for 5 hr. The reaction mixture was concentrated in vacuo and the residue purified by silica gel column chromatography, eluting with 4:1 DCM:ethanol containing 0.5% 880 ammonia, to afford the titled compound as a white solid (0.015 g).

Workup

  1. temperatureunder reflux for 5 hr
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue purified by silica gel column chromatography
  4. washeluting with 4:1 DCM

Sources & evidence

ORD record
ord-de1e478511c54828858e6374f4956ef1
Source dataset
uspto-grants-2005_10
Patent number
US06958344B2

Reaction notes

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