N-(tert-butoxycarbonyl)glycine → ((2S,4R)-4-(2-aminoacetamido)-1-(2-chlorobenzylcarbamoyl)pyrrolidin-2-yl)methyl 4-ethylphenylcarbamate

HRID 655981

Reaktionsgleichung

Reaktionsgleichung von HRID 655981
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:30])[O:11][CH2:12][C@@H:13]2[CH2:17][C@@H:16]([NH2:18])[CH2:15][N:14]2[C:19](=[O:29])[NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])=[CH:5][CH:4]=1)[CH3:2].[NH:31](C(OC(C)(C)C)=O)[CH2:32][C:33](O)=[O:34].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:30])[O:11][CH2:12][C@@H:13]2[CH2:17][C@@H:16]([NH:18][C:33](=[O:34])[CH2:32][NH2:31])[CH2:15][N:14]2[C:19](=[O:29])[NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])=[CH:5][CH:4]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59778486((2S,4R)-4-amino-1-(2-chlorobenzylcarbamoyl)pyrrolidin-2-yl)methyl 4-ethylphenylcarbamate

Produkt 1

HCID 25026415((2S,4R)-4-(2-aminoacetamido)-1-(2-chlorobenzylcarbamoyl)pyrrolidin-2-yl)methyl 4-ethylphenylcarbamateAusbeute 54,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of ((2S,4R)-4-amino-1-(2-chlorobenzylcarbamoyl)pyrrolidin-2-yl)methyl 4-ethylphenylcarbamate (60 mg, 0.14 mmol) in DMF were added Boc-Gly-OH (37 mg, 0.21 mmol) and HBTU (80 mg, 0.21 mmol). The reaction mixture was stirred at rt overnight and purified on RP-HPLC using a mixture of acetonitrile and H2O. The fraction containing the product was combined and concentrated. The residue was dissolved in MeOH and 4N HCl in dioxane. The reaction mixture was stirred at rt for 1 h and concentrated to give ((2S,4R)-4-(2-aminoacetamido)-1-(2-chlorobenzylcarbamoyl)pyrrolidin-2-yl)methyl 4-ethylphenylcarbamate (37 mg, 51%). LRMS (M+H+) m/z 488.1.

Aufarbeitung

  1. custompurified on RP-HPLC
  2. additiona mixture of acetonitrile and H2O
  3. additionThe fraction containing the product
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in MeOH
  6. stirringThe reaction mixture was stirred at rt for 1 h
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d201994f44bb495cb3f625e6f9650642
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071625B2

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