Water → (+/-)-2-(2-bromoethyl)-N-methyl-N-(4-phenoxybenzenesulfonyl)glycine allyl ester

HRID 1838422ノート

反応式

HRID 1838422 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([O:23][C:24](=[O:47])[CH:25]([CH2:44][CH2:45]O)[N:26]([CH3:43])[S:27]([C:30]1[CH:35]=[CH:34][C:33]([O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:32][CH:31]=1)(=[O:29])=[O:28])[CH:21]=[CH2:22].C(Br)(Br)(Br)[Br:49].O>O1CCCC1>[CH2:20]([O:23][C:24](=[O:47])[CH:25]([CH2:44][CH2:45][Br:49])[N:26]([CH3:43])[S:27]([C:30]1[CH:35]=[CH:34][C:33]([O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:32][CH:31]=1)(=[O:29])=[O:28])[CH:21]=[CH2:22]

参加物

6

反応物 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 18753502(+/-)-2-(2-hydroxyethyl)-N-methyl-N-(4-phenoxybenzenesulfonyl)glycine allyl ester

生成物 1

HCID 18753632(+/-)-2-(2-bromoethyl)-N-methyl-N-(4-phenoxybenzenesulfonyl)glycine allyl ester収率 86.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

After triphenylphosphine (4.72 g, 18.0 mmol) was added to a solution of (±)-2-(2-hydroxyethyl)-N-methyl-N-(4-phenoxybenzenesulfonyl)glycine allyl ester (6.08 g, 15.0 mmol), the product of Example 41(2), in tetrahydrofuran (45 ml), a solution of carbon tetrabromide (5.97 g, 18.0 mmol) in tetrahydrofuran (20 ml) was added over 20 minutes to the solution with ice-cooling and with stirring. The mixture was stirred at room temperature for 1 hour. To the reaction mixture, water was added and 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=5/1 as the eluant to afford the desired compound (6.05 g, yield 86%) as a colorless oil.

後処理

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. extractionthis was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column

出典と根拠

ORDレコード
ord-af34643bd05f4683b4b63428bc71cda1
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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