Ethyl bromoacetate → HCID 69755746, 화합물

HRID 2415781노트

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HRID 2415781 반응식
C(=O)([O-])[O-].[K+].[K+].[N+:7]([C:10]1[CH:11]=[CH:12][C:13]2[O:19][CH2:18][CH2:17][CH2:16][NH:15][C:14]=2[CH:20]=1)([O-:9])=[O:8].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>CN(C=O)C>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][N:15]1[C:14]2[CH:20]=[C:10]([N+:7]([O-:9])=[O:8])[CH:11]=[CH:12][C:13]=2[O:19][CH2:18][CH2:17][CH2:16]1)[CH3:27]

참가 물질

5

반응물 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 109871302,3,4,5-Tetrahydro-7-nitro-1,5-benzoxazepine

생성물 1

HCID 69755746HCID 69755746, 화합물수율 50%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

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온도
120 °C

실험 절차

Powdered and flame dried potassium carbonate (1.52 g, 11 mmol, 1.1 eq.) was placed in a round bottom flask together with 60 mL of anhydrous dimethylformamide and kept under inert atmosphere. 2-Nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene (1.942 g, 10 mmol, 1 eq.) was dissolved in 20 mL of anhydrous DMF and added to the reaction mixture. The reaction was heated to 120° C. under reflux condenser for 1 hour and then solution of ethyl bromoacetate (3.34 g, 2.22 mL, 20 mmol, 2 eq.) in 5 mL of dry DMF was added dropwise to the hot solution. The reaction mixture was then heated to 120° C. for an additional 12 hours. When cooled, the DMF was removed on the rotary evaporator, and diluted with 100 mL of water. The aqueous phase was washed (3×) with 50 mL portions of methylene chloride. The methylene chloride extracts were combined and washed with water and brine and dried over magnesium sulfate. Crude material (3.018 g) was chromatographed on a large Biotage column in 20% ethyl acetate/hexanes. 1.38 g (50% yield) of pure material (bright yellow crystalline powder) was collected. LC MS: AP+281, AP−280.

후처리

  1. additionadded to the reaction mixture
  2. temperatureunder reflux condenser for 1 hour
  3. temperatureThe reaction mixture was then heated to 120° C. for an additional 12 hours
  4. temperatureWhen cooled
  5. customthe DMF was removed on the rotary evaporator
  6. additiondiluted with 100 mL of water
  7. washThe aqueous phase was washed (3×) with 50 mL portions of methylene chloride
  8. washwashed with water and brine
  9. dry with materialdried over magnesium sulfate
  10. customCrude material (3.018 g) was chromatographed on a large Biotage column in 20% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-5875fdc206e4445d95a994c428ff6fa8
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06821977B2

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