N-Methoxy-N-methyl-2-phenylacetamide → HCID 66665381、化合物

HRID 872298ノート

反応式

HRID 872298 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]23[CH2:14][CH:12]([CH2:13]2)[O:11][C:10](=[O:15])[NH:9]3)=[CH:4][CH:3]=1.[Li]CCCC.CON(C)[C:24](=[O:32])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1.CCCCCC>[C:26]1([CH2:25][C:24]([C:2]2[CH:7]=[CH:6][C:5]([C:8]34[CH2:14][CH:12]([CH2:13]3)[O:11][C:10](=[O:15])[NH:9]4)=[CH:4][CH:3]=2)=[O:32])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

参加物

6

反応物 3

HCID 10419762N-Methoxy-N-methyl-2-phenylacetamideHCID 58229900HCID 58229900、化合物HCID 178418339Butyllithium2 回

生成物 1

HCID 66665381HCID 66665381、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒2 回

実験手順

A solution of 5-(4-bromo-phenyl)-2-oxa-4-aza-bicyclo[3.1.1]heptan-3-one (prepared according to WO2009/148916, 4 g) in dry THF (60 mL) was cooled to −78° C. and treated with n-BuLi (6.56 mL of a 2.5M solution in hexane) and stirred for 30 minutes at this temperature before addition of further n-BuLi (13.1 mL of a 2.5M solution in hexane). Stirring was continued at this temperature for 30 minutes before a solution of N-methoxy-N-methyl-benzeneacetamide (prepared according to US6407119B1, 4.6 g) in THF (10 mL) was added. After 10 minutes the reaction was quenched with saturated aqueous ammonium chloride solution, extracted with EtOAc and the combined organic phases washed with brine, filtered and concentrated. The residue was triturated with hexane/EtOAc to give the title compound which was used in the next step without further purification.

後処理

  1. additionwas added
  2. customAfter 10 minutes the reaction was quenched with saturated aqueous ammonium chloride solution
  3. extractionextracted with EtOAc
  4. washthe combined organic phases washed with brine
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was triturated with hexane/EtOAc

出典と根拠

ORDレコード
ord-390350192f2947f3b4acc0ccb2377f88
出典データセット
uspto-grants-2015_03
特許番号
US08975265B2

反応ノート

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