HCID 9944444、化合物 → HCID 10272449、化合物

HRID 396403ノート

反応式

HRID 396403 の反応式
[C:1]([NH:8][CH2:9][C:10]#[CH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Li]CCCC.CON(C)[C:20]([C:22]1[O:26][C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N:24][C:23]=1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:21]>C1COCC1>[C:4]([O:3][C:1](=[O:2])[NH:8][CH2:9][C:10]#[C:11][C:20]([C:22]1[O:26][C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N:24][C:23]=1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:21])([CH3:5])([CH3:6])[CH3:7]

参加物

5

反応物 3

HCID 9944444HCID 9944444、化合物HCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 178418339Butyllithium

生成物 1

HCID 10272449HCID 10272449、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-15 °C

実験手順

A −15° C. solution of N-BOC propargyl amine (641 mg, 4.13 mmole, 3.5 eq) in dry THF (12 ml) was treated dropwise with a 1.6M n-BuLi in hexanes solution (5.16 ml, 8.3 mmole, 7.0 eq) and the resulting pale yellow dianion solution stirred at −15° C. for 30 minutes under nitrogen. A dry THF solution (3 ml) of the above-prepared 2,4-Diphenyl-oxazole-5-carboxylic acid methoxy-methyl-amide (365 mg, 1.18 mmole, 1.0 eq) was added dropwise to the dianion solution at −15° C. and the mixture stirred at 0° C. for 2 hours under nitrogen. The mixture was quenched by adding a solution of 2M NaH2PO4 (5 ml), then warmed to room temperature and extracted with ethyl acetate. The organic phase was washed with water and brine then dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a crude brown oil. The crude oil without purification was used immediately in next step.

後処理

  1. stirringthe mixture stirred at 0° C. for 2 hours under nitrogen
  2. customThe mixture was quenched
  3. additionby adding a solution of 2M NaH2PO4 (5 ml)
  4. temperaturewarmed to room temperature
  5. extractionextracted with ethyl acetate
  6. washThe organic phase was washed with water and brine
  7. dry with materialthen dried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d28d5f93e57946f483768dd27e39f48f
出典データセット
uspto-grants-2003_08
特許番号
US06608087B1

反応ノート

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