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1-(3-Amino-3-methylbutyl)-4,4-diethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one → 1-{3-[2-(7-Benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-hydroxyethylamino]-3-methylbutyl}-4,4-diethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one

HRID 2223118
ノート
印刷プレビュー

反応式

HRID 2223118 の反応式
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15](=[O:19])[NH:16]2)=[C:11]([CH:20]2[CH2:22][O:21]2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:23][C:24]([CH3:43])([CH3:42])[CH2:25][CH2:26][N:27]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[C:30]([CH2:39][CH3:40])([CH2:37][CH3:38])[O:29][C:28]1=[O:41]>C(O)(C)C.CCOC(C)=O>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15](=[O:19])[NH:16]2)=[C:11]([CH:20]([OH:21])[CH2:22][NH:23][C:24]([CH3:43])([CH3:42])[CH2:25][CH2:26][N:27]2[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=3[C:30]([CH2:39][CH3:40])([CH2:37][CH3:38])[O:29][C:28]2=[O:41])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 210728171-(3-Amino-3-methylbutyl)-4,4-diethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-oneHCID 574693717-benzyloxy-5-oxiranyl-1H-quinolin-2-one

生成物 1

HCID 210728131-{3-[2-(7-Benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-hydroxyethylamino]-3-methylbutyl}-4,4-diethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒
HCID 8857
Ethyl Acetate
溶媒

実験手順

A suspension of 7-benzyloxy-5-oxiranyl-1H-quinolin-2-one (112 mg, 0.382 mmol) and 1-(3-amino-3-methylbutyl)-4,4-diethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one (220 mg, 0.758 mmol) in isopropanol (1.0 mL) is heated in the microwave for 1 hour to 135° C. The mixture is diluted with EtOAc (10 mL) and washed with 0.5 M aqueous tartaric acid solution, whereupon half the product is precipitated. The phases are separated and the aqueous suspension is combined with MeOH until a clear solution is obtained again. The aqueous phase is extracted with dichloromethane and the combined organic phases are dried with sodium sulfate and evaporated down in vacuo. The residue is stirred with EtOAc and the precipitate is filtered off and dried in vacuo. Yield: 152 mg (68%); HPLC-MS: Rt=14.8 min. (method A).

後処理

  1. temperatureis heated in the microwave for 1 hour to 135° C
  2. washwashed with 0.5 M aqueous tartaric acid solution, whereupon half the product
  3. customis precipitated
  4. customThe phases are separated
  5. customis obtained again
  6. extractionThe aqueous phase is extracted with dichloromethane
  7. dry with materialthe combined organic phases are dried with sodium sulfate
  8. customevaporated down in vacuo
  9. filtrationthe precipitate is filtered off
  10. customdried in vacuo

出典と根拠

ORDレコード
ord-e3ce036c051c49999bf87d0a7232e721
出典データセット
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07375104B2

反応ノート

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