Water → HCID 10230709, 화합물

HRID 844895

반응식

HRID 844895 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]([NH:11][C@H:12]([C:31]([OH:33])=[O:32])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:21](=[O:30])[N:22]([CH3:29])[C:23](=[O:28])[N:24]([CH3:27])[C:25]=2[CH3:26])=[CH:16][CH:15]=1)=[O:10].C(=O)(O)[O-].[Na+].[C:39]([O:42][CH:43](Cl)[CH3:44])(=[O:41])[CH3:40].O>CN(C=O)C>[C:39]([O:42][CH:43]([O:32][C:31](=[O:33])[C@H:12]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[C:21](=[O:30])[N:22]([CH3:29])[C:23](=[O:28])[N:24]([CH3:27])[C:25]=2[CH3:26])=[CH:18][CH:19]=1)[NH:11][C:9]([C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=1[F:8])=[O:10])[CH3:44])(=[O:41])[CH3:40]

참가 물질

6

반응물 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 5218651-Chloroethyl acetateHCID 69337579343850-71-5

생성물 1

HCID 10230709HCID 10230709, 화합물수율 66%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a suspension of N-[(2,6-difluorophenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine (0.743 mmol, 340 mg) and sodium bicarbonate (5.94 mmol, 499 mg) in DMF (3.0 mL) was added 1-chloroethyl acetate (5.94 mmol, 0.73 g) at room temperature. The mixture was stirred for 48 h at room temperature. Then, the reaction mixture was poured into water (50 mL) and was extracted with ethyl acetate (3×25 mL). The combined extracts were washed with brine solution (80 mL) and were dried over anhydrous sodium sulfate. Filtration of the drying agent and concentration of the filtrate gave the crude product which was purified by silica gel chromatography using a Biotage (40m) column to obtain 265 mg (66% yield) of N-[(2,6-difluorophenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine 1-(acetoxy)ethyl ester as an amorphous white solid. ES-HRMS m/e calcd for C27H27F2N3O7 (M+Na) 566.1709, found 566.1710.

후처리

  1. extractionwas extracted with ethyl acetate (3×25 mL)
  2. washThe combined extracts were washed with brine solution (80 mL)
  3. dry with materialwere dried over anhydrous sodium sulfate
  4. filtrationFiltration of the drying agent and concentration of the filtrate
  5. customgave the crude product which
  6. customwas purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-ea99ccc1f846449f9a73b24a70d27196
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06380387B1

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