Lithium hydride → HCID 19390699, compound

HRID 1756593Notes

Reaction equation

HRID 1756593 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[O:28])[N:14]3[C:25]4[C:20](=[CH:21][C:22]([F:26])=[CH:23][CH:24]=4)[C:19](=[O:27])[C:15]3=[N:16]2)=[CH:11][CH:10]=1)=O)(C)([CH3:3])[CH3:2].C(OC[C@@H]1OC1)(=[O:33])CCC.[H-].[Li+]>CN(C=O)C.C(Cl)(Cl)Cl>[OH:33][CH2:2][CH:1]1[O:5][CH2:6][N:8]([C:9]2[CH:18]=[C:17]3[C:12]([C:13](=[O:28])[N:14]4[C:25]5[C:20](=[CH:21][C:22]([F:26])=[CH:23][CH:24]=5)[C:19](=[O:27])[C:15]4=[N:16]3)=[CH:11][CH:10]=2)[CH2:3]1

Participants

6

Reactant 3

HCID 62714Lithium hydrideHCID 2724536(2R)-Oxiran-2-ylmethyl butanoateHCID 19390724HCID 19390724, compound

Product 1

HCID 19390699HCID 19390699, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(N-t-butyloxycarbonylamino)-8-fluoroindolo[2,1-b]quinazoline-6,12-dione (0.5 mmol), (R)-glycidyl butyrate (0.55 mmol) and lithium hydride (0.60 mmol) in DMF is allowed to stir at room temperature overnight. The reaction mixture is diluted with CHCl3, washed with 0.1N HCl, sodium bicarbonate solution, dried (MgSO4) and the solvent is evaporated. Silica gel chromatography (1% MeOH/CHCl3) gives 3-(5-hydroxymethyloxazolidin-3-yl)-8-fluoroindolo[2,1-b]quinazoline-6,12-dione.

Workup

  1. washwashed with 0.1N HCl, sodium bicarbonate solution
  2. dry with materialdried (MgSO4)
  3. customthe solvent is evaporated

Sources & evidence

ORD record
ord-850462d52d074b30bbd74450d2aaad1d
Source dataset
uspto-grants-1995_08
Patent number
US05441955

Reaction notes

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