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L-Glutamine → 4-carbamoyl-2-(6-methoxy-4H-quinazolin-3-yl)butanoic acid

HRID 350611
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HRID 350611 반응식
[CH:1]([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[NH:11][CH:12]=O)=O.[NH2:14][C@H:15]([C:21]([OH:23])=[O:22])[CH2:16][CH2:17][C:18](=[O:20])[NH2:19].[BH4-].[Na+]>CO.[OH-].[Na+]>[C:18]([CH2:17][CH2:16][CH:15]([N:14]1[CH2:1][C:3]2[C:4](=[CH:5][CH:6]=[C:7]([O:9][CH3:10])[CH:8]=2)[N:11]=[CH:12]1)[C:21]([OH:23])=[O:22])(=[O:20])[NH2:19]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 5961L-GlutamineHCID 4311764Sodium borohydrideHCID 21088389N-(2-formyl-4-methoxyphenyl)formamide

생성물 1

HCID 210883854-carbamoyl-2-(6-methoxy-4H-quinazolin-3-yl)butanoic acid

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 14798Sodium Hydroxide
용매
2회

반응 조건

온도
20 °C

실험 절차

A solution of 0.79 g of the product from stage 3 in 30 ml of methanol was added to a solution of 0.58 g of L-glutamine in 10 ml of methanol and 2 ml of 2N sodium hydroxide solution. After stirring for 1 hour at 20° C., the mixture was cooled to 0° C. and 0.103 g of sodium borohydride was added in portions within 30 minutes. The mixture was stirred for 12 hours at 0° C., then adjusted to pH 2 to 3, and stirred for a further 4 hours at 20° C. After neutralizing the solution with sodium hydroxide, the methanol was distilled off. The aqueous residue was washed twice with 15 ml of diethyl ether each time, and then concentrated by evaporation in vacuo. The residue was taken up in 25 ml of methanol and freed from insoluble constituents by filtration. The residue obtained by evaporating the filtrate in vacuo was directly reacted further as described in stage 5, without purification.

후처리

  1. temperaturethe mixture was cooled to 0° C.
  2. stirringThe mixture was stirred for 12 hours at 0° C.
  3. stirringstirred for a further 4 hours at 20° C
  4. distillationthe methanol was distilled off
  5. washThe aqueous residue was washed twice with 15 ml of diethyl ether each time
  6. concentrationconcentrated by evaporation in vacuo
  7. filtrationfreed from insoluble constituents by filtration
  8. customThe residue obtained
  9. customby evaporating the filtrate in vacuo
  10. customas described in stage 5, without purification

출처 및 근거

ORD 기록
ord-be8db5e7db014e8587df42f2c21fd59c
출처 데이터셋
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07183274B2

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