Oxolane--water (1/1) → HCID 86724222, compound

HRID 571997Notes

Reaction equation

[C:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5](=[O:29])[N:6]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:7]([C@@H:13]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH3:14])=[N:8]2)#[N:2].C1C[O:33]CC1.O>>[C:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5](=[O:29])[N:6]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:7]([C@@H:13]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:21])[CH3:19])[CH3:14])=[N:8]2)(=[O:33])[NH2:2]

Participants

Reactant 2

HCID 21881883Oxolane--water (1/1)

HCID 86723620HCID 86723620, compound

Product 1

HCID 86724222HCID 86724222, compound

Conditions

Temperature: 80 °C

Procedure

To a solution of (S)-tert-butyl (1-(5-cyano-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)ethyl)carbamate (105 mg, 0.269 mmol) in THF/H2O (1 mL each) was added Ghaffar's catalyst. The mixture was heated to 80° C. overnight. Purification by flash chromatography (25 g silica, 0-100% EtOAc/DCM) provided (S)-tert-butyl (1-(5-carbamoyl-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)ethyl)carbamate as a white solid. ES/MS 409.1 (M+H+).

Workup

customPurification by flash chromatography (25 g silica, 0-100% EtOAc/DCM)

Sources & evidence

ORD record: ord-88476b7df0bb4710bc0072af1e7c6b5d
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029384B2

Reaction notes

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