Water → HCID 69337137、化合物

HRID 844889

反応式

HRID 844889 の反応式
[CH3:1][C:2]([CH3:30])([O:4][C:5]([NH:7][C@H:8]([C:27]([OH:29])=[O:28])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:17](=[O:26])[N:18]([CH3:25])[C:19](=[O:24])[N:20]([CH3:23])[C:21]=2[CH3:22])=[CH:12][CH:11]=1)=[O:6])[CH3:3].C(=O)(O)[O-].[Na+].[C:36]([O:39][CH:40](Cl)[CH3:41])(=[O:38])[CH3:37].O>CN(C=O)C>[C:36]([O:39][CH:40]([O:28][C:27](=[O:29])[C@H:8]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:17](=[O:26])[N:18]([CH3:25])[C:19](=[O:24])[N:20]([CH3:23])[C:21]=2[CH3:22])=[CH:12][CH:11]=1)[NH:7][C:5]([O:4][C:2]([CH3:30])([CH3:1])[CH3:3])=[O:6])[CH3:41])(=[O:38])[CH3:37]

参加物

6

反応物 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 5218651-Chloroethyl acetateHCID 69337268N-[(1,1-dimethylethoxy)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine

生成物 1

HCID 69337137HCID 69337137、化合物収率 77%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of N-[(1,1-dimethylethoxy)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine (1.006 mmol, 420 mg) and sodium bicarbonate (5.03 mmol, 422 mg) in DMF (8 mL) was added 1-chloroethyl acetate (5.03 mmol, 616 mg) at room temperature. The reaction mixture was stirred for 48 h. Then, it was poured into water (50 mL) and was extracted with ethyl acetate (3×50 mL). The combined extracts were washed with water (2×50 mL) and brine solution (100 mL) and were dried over anhydrous magnesium 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 (40s) column to obtain 390 mg (77% yield) of N-[(1,1-dimethylethoxy)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 C25H33N3O8 (M+Na) 526.2160, found 526.2143.

後処理

  1. extractionwas extracted with ethyl acetate (3×50 mL)
  2. washThe combined extracts were washed with water (2×50 mL) and brine solution (100 mL)
  3. dry with materialwere dried over anhydrous magnesium 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

出典と根拠

ORDレコード
ord-c3ba14a5f8064e1bba4d6ad9bd0ab408
出典データセット
uspto-grants-2002_04
特許番号
US06380387B1

関連ノート

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