HCID 9944444, 화합물 → HCID 10272449, 화합물

HRID 585116노트

반응식

HRID 585116 반응식
[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]

참가 물질

5

반응물 3

HCID 9944444HCID 9944444, 화합물HCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 178418339Butyllithium

생성물 1

HCID 10272449HCID 10272449, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-15 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-08c8afafcefb42cfa5bbbc7ae6ab2831
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06930116B2

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