Tyrosine Methyl Ester → O-(tert-butyldiphenylsilyl)-L-tyrosine methyl ester

HRID 850142

反応式

HRID 850142 の反応式
[CH3:1][O:2][C:3](=[O:14])[C@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[NH2:5].C(N(C(C)C)CC)(C)C.[Si:24](Cl)([C:37]([CH3:40])([CH3:39])[CH3:38])([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:14])[C@H:4]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][Si:24]([C:37]([CH3:40])([CH3:39])[CH3:38])([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:11][CH:12]=1)[NH2:5]

参加物

5

反応物 3

HCID 70652Tyrosine Methyl EsterHCID 81531DiisopropylethylamineHCID 94078tert-Butyldiphenylchlorosilane

生成物 1

HCID 53905505O-(tert-butyldiphenylsilyl)-L-tyrosine methyl ester収率 87.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of L-tyrosine methyl ester (Sigma Chemical Company) (10.0 g, 51.3 mmol) and diisopropylethylamine (25.9 g, 200.0 mmol) in CH2Cl2 (400 mL) was added t-butyldiphenylsilyl chloride (TBDPS-Cl; 35.2 g, 128.2 mmol) at 23° C. The resultant mixture was stirred at 23° C. for 14 hours. The crude reaction mixture was dried over (MgSO4) and concentrated in vacuo. The resultant residue was purified by silica gel flash column chromatography. The polarity of the eluting solvent mixture was adjusted according to the Rf value of the product. The eluted fractions were combined, dried over MgSO4, concentrated and dried to give 19.5 g (87.8% yield) of O-(tert-butyldiphenylsilyl)-L-tyrosine methyl ester as a colorless syrup. Rf (hexanes/ethyl acetate (AcOEt)/methanol (MeOH) 20:20:1)=0.38.

後処理

  1. customThe crude reaction mixture
  2. dry with materialwas dried over (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue was purified by silica gel flash column chromatography
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customdried

出典と根拠

ORDレコード
ord-87039577dfd94d8998a5be8198a65934
出典データセット
uspto-grants-2000_01
特許番号
US06015887

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