6-amino-3,4-dihydro-2H-1,4-benzoxazin-3-one → 6-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-propylamino]-4H-benzo[1,4]oxazin-3-one

HRID 1801469Notes

Reaction equation

[C:1]([Si:5]([CH3:12])([CH3:11])[O:6][CH2:7][C@@H:8]1[CH2:10][O:9]1)([CH3:4])([CH3:3])[CH3:2].[NH2:13][C:14]1[CH:15]=[CH:16][C:17]2[O:22][CH2:21][C:20](=[O:23])[NH:19][C:18]=2[CH:24]=1>CC#N>[C:1]([Si:5]([CH3:12])([CH3:11])[O:6][CH2:7][C@@H:8]([OH:9])[CH2:10][NH:13][C:14]1[CH:15]=[CH:16][C:17]2[O:22][CH2:21][C:20](=[O:23])[NH:19][C:18]=2[CH:24]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of tert-butyl-dimethyl-((5)-1-oxiranylmethoxy)-silane (commercial; 10.0 g, 53 mmol) in MeCN (160 mL) was added LiClO4 (16.9 g, 159 mmol). 6-amino-4H-benzo[1,4]oxazin-3-one (commercial; 8.72 g, 53.1 mmol) was added and the mixture was stirred at 50° C. for 6 h. The solvent was removed in vacuo and the residue was purified by FC (DCM/MeOH/NH4OH 1000:25:2 to 1000:100:2) to afford the title compound as a pale brown foam (10.24 g, 55% yield).

Workup

customThe solvent was removed in vacuo
customthe residue was purified by FC (DCM/MeOH/NH4OH 1000:25:2 to 1000:100:2)

Sources & evidence

ORD record: ord-e0a3561eb76a40268e6b1eaf4c528fd2
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349828B2

Reaction notes

Loading…