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Methyl chloroformate → 1-(3,5-difluorophenyl)-2-(2,3-dihydro-6-methoxycarbonylmethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropan-1-one

HRID 1274864
ノート
印刷プレビュー

反応式

HRID 1274864 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[F:11][C:12]1[CH:13]=[C:14]([C:19](=[O:37])[C:20]([N:23]2[C:28](=[O:29])[C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:26]([CH3:36])[O:25][CH2:24]2)([CH3:22])[CH3:21])[CH:15]=[C:16]([F:18])[CH:17]=1.Cl[C:39]([O:41][CH3:42])=[O:40]>O1CCCC1>[F:11][C:12]1[CH:13]=[C:14]([C:19](=[O:37])[C:20]([N:23]2[C:28](=[O:29])[C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:26]([CH2:36][C:39]([O:41][CH3:42])=[O:40])[O:25][CH2:24]2)([CH3:22])[CH3:21])[CH:15]=[C:16]([F:18])[CH:17]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6586Methyl chloroformateHCID 2733832Lithium HexamethyldisilazideHCID 221182601-(3,5-difluorophenyl)-2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methyl-propan-1-one

生成物 1

HCID 221182741-(3,5-difluorophenyl)-2-(2,3-dihydro-6-methoxycarbonylmethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropan-1-one収率 11.2%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
20 °C

実験手順

Lithium bis(trimethylsilyl)amide (1.5 ml of 1.0M solution) was added to a solution of 1-(3,5-difluorophenyl)-2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methyl-propan-1-one (0.5 g) in tetrahydrofuran, under an inert atmosphere at -5° C. After stirring for 0.5 hours, methyl chloroformate (1.22 g) was added and the solution allowed to warm to 20° C. After 18 hours, the solution was poured onto water, extracted (ether) and evaporated. Purification by dry column chromatography on silica gel, eluting with hexane/ethyl acetate (4:1), gave 1-(3,5-difluorophenyl)-2-(2,3-dihydro-6-methoxycarbonylmethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropan-1-one (Compound 700, 0.065 g), NMR 1.5 (s,6H), 3.1 (s,2H), 3.6 (s,3H), 5.4 (s,2H), 6.8 (m,1H), 7.0 (m,2H), 7.2 (m,3H), 7.5 (d,2H).

後処理

  1. waitAfter 18 hours
  2. additionthe solution was poured onto water
  3. extractionextracted (ether)
  4. customevaporated
  5. customPurification
  6. customby dry column chromatography on silica gel
  7. washeluting with hexane/ethyl acetate (4:1)

出典と根拠

ORDレコード
ord-750a4d3e084b47a492ee5e71e12e0be9
出典データセット
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06159902

反応ノート

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