Hydrogen Peroxide → Acetate

HRID 861943Notes

Reaction equation

HRID 861943 reaction equation
[CH:1]1[C:11]2[N:10]3[CH:12]=[C:13]4[C:18](=[N:19][C:9]3=[CH:8][N:7]([CH2:20][CH2:21][C:22]([OH:24])=[O:23])[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1)[CH:17]=[CH:16][CH:15]=[CH:14]4.O.OO.[OH-].[Li+]>C1COCC1>[CH:1]1[C:11]2[N:10]3[CH:12]=[C:13]4[C:18](=[N:19][C:9]3=[CH:8][N:7]([CH2:20][CH2:21][C:22]([OH:24])=[O:23])[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1)[CH:17]=[CH:16][CH:15]=[CH:14]4.[C:22]([O-:24])(=[O:23])[CH3:21]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 3939Lithium HydroxideHCID 19700579HCID 19700579, compound

Product 2

HCID 175AcetateYield 10%HCID 19700579HCID 19700579, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Quinazolino[3,2-a][1,4]benzodiazepine-6(5H)-propanoic acid, 3-[[4-(aminoiminomethyl)phenyl]methoxy]-7,13-dihydro-5,13-dioxo, acetate was prepared by disolving quinazolino[3,2-a][1,4]benzodiazepine-6(5H)-propanoic acid, 3-[[4-(iminoaminomethyl)phenyl]methoxy]-7,13-dihydro-5,13-dioxo, ethyl ester (50 mgs, 0.085 mmol), in 4 mL THF and 2 mL water at room temperature and sequentally adding 0.77 mL 30% solution of hydrogen peroxide (9× excess) and 0.006 grams lithium hydroxide (0.256 mmol, 3× excess). The mixture was stirred for 2 hours, quenched with a saturated solution of sodium bisufite and 0.25 mL glacial acetic acid. The mixture was concentrated in vacuo and purified by HPLC (solvent gradient 1:4 acetonitrile:water(0.5% acetic acid) (time 0 to 10 mins.) to 3:2 acetonitrile:water(0.5% acetic acid) (time 50 mins.), 20 mL/min, C18 2" column) to yield quinazolino[3,2-a][1,4]benzodiazepine-6(5H)-propanoic acid, 3-[[4-(aminoiminomethyl)phenyl]methoxy]-7,13-dihydro-5,13-dioxo, acetate (0.005 grams, 10%).

Workup

  1. customQuinazolino[3,2-a][1,4]benzodiazepine-6(5H)-propanoic acid, 3-[[4-(aminoiminomethyl)phenyl]methoxy]-7,13-dihydro-5,13-dioxo, acetate was prepared
  2. customquenched with a saturated solution of sodium bisufite and 0.25 mL glacial acetic acid
  3. concentrationThe mixture was concentrated in vacuo
  4. custompurified by HPLC (solvent gradient 1:4 acetonitrile:water(0.5% acetic acid) (time 0 to 10 mins.) to 3:2 acetonitrile:water(0.5% acetic acid) (time 50 mins.), 20 mL/min, C18 2" column)

Sources & evidence

ORD record
ord-6d3b19c41c4d4074985fe4afd1a77c70
Source dataset
uspto-grants-1998_02
Patent number
US05716951

Reaction notes

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