(S)-2-tert-butoxycarbonylamino-3-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid methyl ester → 3-[(9H-fluoren-9-ylmethoxy)carbonyl]amino-L-alanine, methyl ester

HRID 1352068노트

반응식

HRID 1352068 반응식
CC(C)(OC([NH:7][C@H:8]([C:28]([O:30][CH3:31])=[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)C>FC(F)(F)C(O)=O.ClCCl>[CH:17]1[C:16]2[CH:15]([CH2:14][O:13][C:11]([NH:10][CH2:9][C@@H:8]([C:28]([O:30][CH3:31])=[O:29])[NH2:7])=[O:12])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]=2[CH:20]=[CH:19][CH:18]=1

참가 물질

3

반응물 1

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

생성물 1

HCID 695121003-[(9H-fluoren-9-ylmethoxy)carbonyl]amino-L-alanine, methyl ester

시약·촉매·용매 1

HCID 21863450Trifluoroacetic acid methylene chloride용매

실험 절차

A solution of N-[(1,1-dimethylethoxy)carbonyl]-3-[(9H-fluoren-9-ylmethoxy)carbonyl]amino-L-alanine, methyl ester (Example 62; 200 mg, 0.45 mmol) in trifluoroacetic acid/dichloromethane (1:1; 2 mL) was stirred at room temperature for 40 min. The solvent was evaporated and ethyl acetate (10 mL) was added. The solution was washed with saturated aqueous sodium hydrogen carbonate, dried (Na2SO4), filtered and evaporated to give 3-[(9H-fluoren-9-ylmethoxy)carbonyl]amino-L-alanine, methyl ester. HOAT (73 mg, 0.45 mmol), DCC (111 mg, 0.45 mmol), 2-chloro-4-[[(1H-indol-4-ylmethyl)amino]carbonyl]-benzoic acid (Example 36; 148 mg, 0.45 mmol) and N,N-dimethylformamide (5 mL) were added and the solution was stirred at room temperature for 1.5 h. Water was added and the solution was extracted three times with ethyl acetate. The combined extracts were washed with brine, dried (Na2SO4), filtered, evaporated, and chromatographed (40–80% ethyl acetate/hexanes) to give 3-[(9H-fluoren-9-ylmethoxy)carbonyl]amino-N-[2-chloro-4-[[(1H-indol-4-ylmethyl)amino]carbonyl]benzoyl]-L-alanine, methyl ester (116 mg, 40%).

후처리

  1. customThe solvent was evaporated
  2. additionethyl acetate (10 mL) was added
  3. washThe solution was washed with saturated aqueous sodium hydrogen carbonate
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-0144d59eb26e4713914aa20d40796d21
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07217728B2

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