Diisopropylethylamine → 4-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester

HRID 446958

Reaktionsgleichung

Reaktionsgleichung von HRID 446958
[CH3:1][C:2]([O:5][C:6]([NH:8][C@H:9]([C:16]([OH:18])=O)[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:7])([CH3:4])[CH3:3].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.[CH3:52][O:53][C:54]([CH:56]1[CH2:60][N:59]([C:61]([O:63][CH2:64][C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)=[O:62])[CH:58]2[CH2:71][CH2:72][NH:73][CH:57]12)=[O:55]>CN1C(=O)CCC1.CCOC(C)=O>[CH3:52][O:53][C:54]([CH:56]1[CH2:60][N:59]([C:61]([O:63][CH2:64][C:65]2[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=2)=[O:62])[CH:58]2[CH2:71][CH2:72][N:73]([C:16](=[O:18])[CH:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]3)[CH:57]12)=[O:55]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 7004938N-(tert-Butoxycarbonyl)-L-cyclohexylglycineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67281633HCID 67281633, Verbindung

Produkt 1

HCID 672814894-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1,3-dicarboxylic acid 1-benzyl ester 3-methyl esterAusbeute 106,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel2×

Versuchsvorschrift

A solution of Boc-L-cyclohexylglycine (257 mg, 1 mmol) in NMP (5 mL) was cooled to 0° C. and treated with HATU (380 mg, 1 mmol) followed by DIPEA (0.3 mL, 1.7 mmol). After 10 min, 15 (309 mg, 1.0 mmol) in NMP (5 mL) was added. The reaction mixture was allowed to warm to ambient temperature overnight. The solution was diluted with EtOAc, washed successively with 1M HCl, saturated NaHCO3, dried over anhydrous Na2SO4, filtered and concentrated to afford 16 as an orange-colored foam (578 mg) which was used without further purification. Mass spectrum, m/z [544.4] (M+H)+.

Aufarbeitung

  1. washwashed successively with 1M HCl, saturated NaHCO3
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a34612f279514ad5b5d29c3cc47dcaac
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481495B2

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