Trifluoroacetic acid → Methyl D-Tryptophanate

HRID 1018464ノート

反応式

HRID 1018464 の反応式
[CH3:1][O:2][C:3](=[O:23])[C@H:4]([NH:15]C(OC(C)(C)C)=O)[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1.FC(F)(F)C(O)=O>>[CH3:1][O:2][C:3](=[O:23])[C@H:4]([NH2:15])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1

参加物

3

反応物 2

HCID 6422Trifluoroacetic acidHCID 7188267N-[(1,1-Dimethylethoxy)carbonyl]-D-tryptophan methyl ester

生成物 1

HCID 168016Methyl D-Tryptophanate

実験手順

To 4.92 g (16.2 mmol) of N-α-t-BOC-D-tryptophan in 100 mL of DMF was added 2.46 g (17.8 mmol) of potassium carbonate followed by 2.41 g (17.0 mmol) of iodomethane, and the mixture was stirred overnight at 24° C. under an atmosphere of nitrogen. The reaction mixture was diluted with water, and extracted three times with ethyl acetate. The combined organics were washed five times with 500 mL of water and once with brine, dried over MgSO4 and concentrated to give 4.67 g of a white solid. To the crude (R)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionic acid methyl ester was added 15 mL of cold trifluoroacetic acid at about 0° C. and the mixture was stirred for about 2 h. The mixture was concentrated and the residue was diluted with 1N NaOH and extracted three times with ethyl acetate. The combined organic extracts were washed with brine and dried over Na2SO4 to give (R)-2-amino-3-(1H-indol-3-yl)-propionic acid methyl ester as an orange oil in quantitative yield.

後処理

  1. concentrationThe mixture was concentrated
  2. additionthe residue was diluted with 1N NaOH
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4

出典と根拠

ORDレコード
ord-d7137b4c90024186a1954ea18cf9cf4f
出典データセット
uspto-grants-2002_11
特許番号
US06482825B2

反応ノート

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