Trifluoroacetic acid → Methyl D-Tryptophanate

HRID 1018464

반응식

HRID 1018464 반응식
[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

참가 물질

3

반응물 2

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

생성물 1

HCID 168016Methyl D-Tryptophanate

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d7137b4c90024186a1954ea18cf9cf4f
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06482825B2

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