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 1640548Notes

Reaction equation

HRID 1640548 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1.[C:13]([Si:17]([CH3:24])([CH3:23])[O:18][CH2:19][C@@H:20]1[CH2:22][O:21]1)([CH3:16])([CH3:15])[CH3:14]>>[C:13]([Si:17]([CH3:24])([CH3:23])[O:18][CH2:19][C@@H:20]([OH:21])[CH2:22][NH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1)([CH3:14])([CH3:16])[CH3:15]

Participants

3

Reactant 2

HCID 27636816-amino-3,4-dihydro-2H-1,4-benzoxazin-3-oneHCID 10954307(S)-Glycidoxy-t-butyldimethylsilane

Product 1

HCID 667376956-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-propylamino]-4H-benzo[1,4]oxazin-3-one

Procedure

Starting from 6-amino-4H-benzo[1,4]oxazin-3-one and tert-butyl-dimethyl-((S)-1-oxiranylmethoxy)-silane and using a procedure analogous to that of Example 201, step 201.ii, the title compound was obtained as a pale brown foam (5.2 g, 66% yield).

Sources & evidence

ORD record
ord-a64130342fa248639223cd0c8669f061
Source dataset
uspto-grants-2012_02
Patent number
US08114867B2

Reaction notes

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