Water → (S)-2-tert-butoxycarbonylamino-3-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid methyl ester

HRID 1726758노트

반응식

HRID 1726758 반응식
[CH3:1][C:2]([CH3:31])([O:4][C:5]([NH:7][C@H:8]([C:28]([OH:30])=[O:29])[CH2:9][NH:10][C:11]([O:13][CH2:14][CH:15]1[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])=[O:6])[CH3:3].[C:32](=O)([O-])O.[K+].IC.O>CN(C)C=O>[CH3:3][C:2]([CH3:31])([O:4][C:5]([NH:7][C@H:8]([C:28]([O:30][CH3:32])=[O:29])[CH2:9][NH:10][C:11]([O:13][CH2:14][CH:15]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=2[C:22]2[C:27]1=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:12])=[O:6])[CH3:1]

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 516893Potassium BicarbonateHCID 7019527(2S)-2-(((tert-butoxy)carbonyl)amino)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)propanoic acid

생성물 1

HCID 59977282(S)-2-tert-butoxycarbonylamino-3-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid methyl ester수율 81.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of N-[(1,1-dimethylethoxy)carbonyl]-3-[(9H-fluoren-9-ylmethoxy)carbonyl]amino-L-alanine (5.00 g, 11.7 mmol) in N,N-dimethylformamide (10 mL) was treated with potassium hydrogen carbonate (1.4 g, 14.1 mmol) and iodomethane (0.8 ml, 12.9 mmol). The reaction mixture was stirred at room temperature for 2 h. Then water was added and the mixture was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried (Na2SO4), concentrated and chromatographed (10-40% ethyl acetate/hexanes) to give N-[(1,1-dimethylethoxy)carbonyl]-3-[(9H-fluoren-9-ylmethoxy)carbonyl]amino-L-alanine, methyl ester (4.20 g, 81%) as a white solid.

후처리

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customchromatographed (10-40% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-13ff27bb4d624ab68ed77fc7398c993b
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07491741B2

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