Methanol → HCID 70059047、化合物

HRID 2230273

反応式

HRID 2230273 の反応式
[CH3:1][C@@:2]([C:12]([OH:14])=[O:13])([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[NH2:3].CO.[CH2:17]([Br:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>[OH-].[Na+].[O-]S([O-])(=O)=O.[Cu+2]>[BrH:24].[NH2:3][C:2]([CH3:1])([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:7][CH:6]=1)[C:12]([OH:14])=[O:13]

参加物

6

反応物 3

HCID 887MethanolHCID 7498Benzyl BromideHCID 441350Metyrosine

生成物 1

HCID 70059047HCID 70059047、化合物収率 46.4%

試薬・触媒・溶媒 2

HCID 24462Copper Sulfate触媒HCID 14798Sodium Hydroxide溶媒

実験手順

A solution of α-methyltyrosine (Aldrich Chemical Co., 10.0 g, 51.2 mmol) in 50 mL of 2N NaOH solution was treated with 40 mL of a 0.5 M solution of aqueous CuSO4. The resulting solution was stirred for 45 minutes. The resulting solution was treated with 150 mL of methanol and benzyl bromide (6.7 mL, 56.3 mmol) and stirred for an additional 45 minutes at 50° C. The light purple precipitate which formed was collected by suction filtration and dried under vacuum. The isolated solid was suspended in water and treated with 13 mL of concentrated hydrochloric acid. The suspended solid was collected by filtration, washed sequentially with 1N HCl solution and ether and then dried under vacuum at 45° C. (96 hr) to give the product as an off-white solid (8.7 g, 46%), mp=228-231° C. (dec).

後処理

  1. stirringstirred for an additional 45 minutes at 50° C
  2. customThe light purple precipitate which formed
  3. filtrationwas collected by suction filtration
  4. customdried under vacuum
  5. additiontreated with 13 mL of concentrated hydrochloric acid
  6. filtrationThe suspended solid was collected by filtration
  7. washwashed sequentially with 1N HCl solution and ether
  8. customdried under vacuum at 45° C. (96 hr)

出典と根拠

ORDレコード
ord-51dd80ddf1a143069dc35a0ceaa7ab65
出典データセット
uspto-grants-2002_07
特許番号
US06423689B1

関連ノート

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