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 1259834

反応式

HRID 1259834 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 667376956-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-propylamino]-4H-benzo[1,4]oxazin-3-one収率 49.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

To a solution of tert-butyl-dimethyl-((S)-1-oxiranylmethoxy)-silane (commercial; 13.0 g, 69 mmol) in MeCN (220 mL) was added LiClO4 (22 g, 207 mmol). 6-amino-4H-benzo[1,4]oxazin-3-one (commercial; 11.45 g, 64 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 CC (DCM/MeOH/NH4OH 1000/25/2 to 1000/100/2) to afford the title intermediate as a pale brown foam (11.16 g, 44% yield).

後処理

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

出典と根拠

ORDレコード
ord-9ed9890e33ac4d40be18c75db3f7c8bd
出典データセット
uspto-grants-2013_06
特許番号
US08466168B2

関連ノート

読み込み中…