tert-Butyl bromoacetate → t-Butyl (5-nitro-1-methyl-uracilyl)acetate

HRID 1251358노트

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HRID 1251358 반응식
[N+:1]([C:4]1[C:5](=[O:12])[NH:6][C:7](=[O:11])[N:8]([CH3:10])[CH:9]=1)([O-:3])=[O:2].Br[CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]>O>[N+:1]([C:4]1[C:5](=[O:12])[N:6]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:7](=[O:11])[N:8]([CH3:10])[CH:9]=1)([O-:3])=[O:2]

참가 물질

4

반응물 2

HCID 79177tert-Butyl bromoacetateHCID 27557345-Nitro-1-methyl-uracil

생성물 1

HCID 53829665t-Butyl (5-nitro-1-methyl-uracilyl)acetate수율 59%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Sodium hydride (0.51 g of a 60% dispersion in mineral oil, 13 mmol) was washed with pentane three times (4 mL each). The compound of Example 109 (2.00 g, 12 mmole) was added portionwise. After the addition was complete, the reaction mixture was stirred for 30 minutes under a nitrogen atmosphere. t-Butyl bromoacetate (1.73 g, 12 mmole) was added in one portion, and the solution was stirred for 3 hours. The reaction mixture was diluted with water (200 mL), and extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with water (3×50 mL), then brine, dried over magnesium sulfate. The solvent was concentrated, hexanes were added and the solvent was removed in vacuo to afford the title compound (1.97 g) in 59% yield. Rf=0.38 (silica gel, 20% ethyl acetate in dichloromethane.

후처리

  1. washSodium hydride (0.51 g of a 60% dispersion in mineral oil, 13 mmol) was washed with pentane three times (4 mL each)
  2. additionAfter the addition
  3. stirringthe solution was stirred for 3 hours
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. washThe combined organic extracts were washed with water (3×50 mL)
  6. dry with materialbrine, dried over magnesium sulfate
  7. concentrationThe solvent was concentrated
  8. additionhexanes were added
  9. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-9de6b4fea52b4c9f91389085fc5c8ade
출처 데이터셋
uspto-grants-2002_01
특허 번호
US06342504B1

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