Benzyl Bromide → methyl O-benzyl-N-trityl-L-serinate

HRID 221568ノート

反応式

HRID 221568 の反応式
[C:1]([NH:20][C@H:21]([C:24]([O:26][CH3:27])=[O:25])[CH2:22][OH:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)Cl.[Cl-].C([N+](C)(C)C)C1C=CC=CC=1>[CH2:30]([O:23][CH2:22][C@@H:21]([C:24]([O:26][CH3:27])=[O:25])[NH:20][C:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

参加物

6

反応物 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 7128367N-(Triphenylmethyl)-L-serine methyl ester

生成物 1

HCID 67156483methyl O-benzyl-N-trityl-L-serinate収率 71.3%

試薬・触媒・溶媒 2

HCID 5963Benzyltrimethylammonium chloride触媒HCID 6344Dichloromethane溶媒2 回

実験手順

Methyl N-trityl-L-serinate (3.61 g, 10.0 mmol), prepared by the method of Baldwin, Tetrahedron, 49, pp. 6309-6330, (1993), was dissolved in 50 mL of CH2Cl2 followed by the addition of 25 mL of 50% aqueous NaOH solution. To the stirred mixture were added benzyltrimethylammonium chloride (186 mg, 1.00 mmol) and benzyl bromide (1.20 mL, 10.0 mmol). After stirring overnight, the mixture was treated with 100 mL of ice water. After all of the ice had melted, 100 mL of CH2Cl2 was added and the layers were separated. The aqueous portion was extracted with another 50 mL of CH2Cl2 and the combined organic layers were washed with H2O (2×100 mL) and brine (3×50 mL). The organic portion was dried over Na2SO4, filtered and concentrated. Chromatography (SiO2, 10-20% ethyl acetate/hexanes) gave 3.22 g of methyl O-benzyl-N-trityl-L-serinate as a colorless syrup.

後処理

  1. customthe layers were separated
  2. extractionThe aqueous portion was extracted with another 50 mL of CH2Cl2
  3. washthe combined organic layers were washed with H2O (2×100 mL) and brine (3×50 mL)
  4. dry with materialThe organic portion was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-c1e2f3844de94f07a86afb60db67a172
出典データセット
uspto-grants-2012_06
特許番号
US08207162B2

反応ノート

読み込み中…