Diisopropylethylamine → 4-(3-tert-Butoxy-2-tert-butoxycarbonylamino-butyryl)-3-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

HRID 1949628노트

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HRID 1949628 반응식
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([OH:12])=O)[C@@H:3]([CH3:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH2:53]([O:60][C:61]([N:63]1[CH2:67][CH:66]([C:68]2[C:76]3[C:71](=[CH:72][C:73]([F:77])=[CH:74][CH:75]=3)[NH:70][CH:69]=2)[CH:65]2[NH:78][CH2:79][CH2:80][CH:64]12)=[O:62])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>CN1C(=O)CCC1.CCOC(C)=O>[CH2:53]([O:60][C:61]([N:63]1[CH2:67][CH:66]([C:68]2[C:76]3[C:71](=[CH:72][C:73]([F:77])=[CH:74][CH:75]=3)[NH:70][CH:69]=2)[CH:65]2[N:78]([C:10](=[O:12])[CH:2]([NH:1][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:3]([O:4][C:5]([CH3:6])([CH3:7])[CH3:8])[CH3:9])[CH2:79][CH2:80][CH:64]12)=[O:62])[C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 7015770(2S,3R)-3-(tert-butoxy)-2-(((tert-butoxy)carbonyl)amino)butanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 672129273-(6-Fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

생성물 1

HCID 674094014-(3-tert-Butoxy-2-tert-butoxycarbonylamino-butyryl)-3-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매2회

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온도
0 °C

실험 절차

To a solution containing Boc-Thr(tBu)-OH (138 mg, 0.5 mmol) in anhydrous NMP (4 mL) was cooled to 0° C. HATU (190 mg, 0.5 mmol) and DIPEA (111 mg, 0.8 mmol) were added followed by the addition of crude 42 (195 mg, 0.5 mmol) in anhydrous NMP (5 mL). The reaction mixture was slowly warmed to ambient temperature. After 4 h, the reaction mixture was diluted with EtOAc and washed successively with 1M HCl, aqueous NaHCO3, and brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 336 mg of crude 43 as an amber-colored foam which was used without further purification. Mass spectrum, m/z [637.3] (M+H)+.

후처리

  1. temperatureThe reaction mixture was slowly warmed to ambient temperature
  2. washwashed successively with 1M HCl, aqueous NaHCO3, and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e445000a52c04e2caa3302d6776f8c30
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399683B2

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