Theobromine → (+/-)-2-[2-(3,7-Dimethylxanthin-1-yl)ethyl]-n-methyl-n-(4-phenoxybenzene-sulfonyl)glycine allyl ester

HRID 1838423ノート

反応式

HRID 1838423 の反応式
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][N:7]([CH3:11])[C:6]=2[C:5](=[O:12])[NH:4][C:3]1=[O:13].[H-].[Na+].[CH2:16]([O:19][C:20](=[O:43])[CH:21]([CH2:40][CH2:41]Br)[N:22]([CH3:39])[S:23]([C:26]1[CH:31]=[CH:30][C:29]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:28][CH:27]=1)(=[O:25])=[O:24])[CH:17]=[CH2:18].[Cl-].[NH4+]>CN(C)C=O>[CH2:16]([O:19][C:20](=[O:43])[CH:21]([CH2:40][CH2:41][N:4]1[C:5](=[O:12])[C:6]2[N:7]([CH3:11])[CH:8]=[N:9][C:10]=2[N:2]([CH3:1])[C:3]1=[O:13])[N:22]([CH3:39])[S:23]([C:26]1[CH:31]=[CH:30][C:29]([O:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[CH:28][CH:27]=1)(=[O:25])=[O:24])[CH:17]=[CH2:18]

参加物

6

反応物 4

HCID 5429TheobromineHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 18753632(+/-)-2-(2-bromoethyl)-N-methyl-N-(4-phenoxybenzenesulfonyl)glycine allyl ester

生成物 1

HCID 18753500(+/-)-2-[2-(3,7-Dimethylxanthin-1-yl)ethyl]-n-methyl-n-(4-phenoxybenzene-sulfonyl)glycine allyl ester収率 30.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
50 °C

実験手順

After addition of 3,7-dimethylxanthin (1.10 g, 6.1 mmol) to a suspension of sodium hydride (60%, 0.24 g, 6.0 mmol) in N,N-dimethylformamide (20 ml), the mixture was stirred at 50° C. for 2 hours. After cooling it to room temperature, a solution of (±)-2-(2-bromoethyl)-N-methyl-N-(4-phenoxybenzenesulfonyl)glycine allyl ester (2.34 g, 5.0 mmol) in N,N-dimethylformamide (10 ml) was added to the reaction mixture. This was heated at 80° C. for 2 hours. After cooling it to room temperature, a saturated aqueous solution of ammonium chloride was added and then this was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate 3/1 as the eluant to afford the desired compound (0.86 g, yield 30%) as a colorless amorphous solid.

後処理

  1. temperatureAfter cooling it to room temperature
  2. temperatureThis was heated at 80° C. for 2 hours
  3. temperatureAfter cooling it to room temperature
  4. extractionthis was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography on a silica gel column

出典と根拠

ORDレコード
ord-ac727818fd294cfba28849e733be6550
出典データセット
uspto-grants-2004_01
特許番号
US06673804B1

反応ノート

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