Ammonium formate → tert-butyl (2R)-2-{[(3-{[(2,2-dimethylpropanoyl)oxy]methyl}-7-hydroxy-4-oxo-3,4-dihydroquinazolin-5-yl)oxy]methyl}pyrrolidine-1-carboxylate

HRID 640013Notes

Reaction equation

C([O-])=O.[NH4+].C([O:12][C:13]1[CH:22]=[C:21]2[C:16]([C:17](=[O:31])[N:18]([CH2:23][O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])[CH:19]=[N:20]2)=[C:15]([O:32][CH2:33][C@H:34]2[CH2:38][CH2:37][CH2:36][N:35]2[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH:14]=1)C1C=CC=CC=1>[Pd].C(OCC)(=O)C>[CH3:27][C:26]([CH3:29])([CH3:28])[C:25]([O:24][CH2:23][N:18]1[C:17](=[O:31])[C:16]2[C:21](=[CH:22][C:13]([OH:12])=[CH:14][C:15]=2[O:32][CH2:33][C@H:34]2[CH2:38][CH2:37][CH2:36][N:35]2[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[N:20]=[CH:19]1)=[O:30]

Participants

Conditions

Temperature: 70 °C

Procedure

Ammonium formate (1.80 g, 28 mmol) and 10% palladium on carbon (0.180 g) were added to a solution of tert-butyl (2R)-2-{[(7-(benzyloxy)-3-{[(2,2-dimethylpropanoyl)oxy]methyl}-4-oxo-3,4-dihydroquinazolin-5-yl)oxy]methyl}pyrrolidine-1-carboxylate (1.58 g, 2.8 mmol) in ethyl acetate (30 ml) and the mixture stirred at 70° C. for 24 hours. The mixture was filtered through Celite and then evaporated under reduced pressure. The residue was purified by silica gel chromatography eluting with a 0 to 10% mixture methanol in dichloromethane to give tert-butyl (2R)-2-{[(3-{[(2,2-dimethylpropanoyl)oxy]methyl}-7-hydroxy-4-oxo-3,4-dihydroquinazolin-5-yl)oxy]methyl}pyrrolidine-1-carboxylate (0.750 g, 52% yield):

Workup

filtrationThe mixture was filtered through Celite
customevaporated under reduced pressure
customThe residue was purified by silica gel chromatography
washeluting with a 0 to 10% mixture methanol in dichloromethane

Sources & evidence

ORD record: ord-c6349daeb90e4f5483c338146271b4e0
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691867B2

Reaction notes

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