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Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 178502742, Verbindung

HRID 367042
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 367042
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]([NH2:29])=[N:13][CH2:14][CH2:15][CH2:16][C@H:17]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:18](O)=[O:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:30][NH:31][O:32][CH3:33].Cl.CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[NH:21]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[C@H:17]([C:18]([N:31]([O:32][CH3:33])[CH3:30])=[O:19])[CH2:16][CH2:15][CH2:14][NH:13][C:12](=[NH:29])[NH:11][S:8]([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=1)(=[O:10])=[O:9]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 83767L-Ornithine, N2-[(1,1-dimethylethoxy)carbonyl]-N5-[imino[[(4-methylphenyl)sulfonyl]amino]methyl]-HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Produkt 1

HCID 178502742HCID 178502742, Verbindung
Ausbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of Boc-Arg(Tos)- OH (2 g, 4.7 mmol) in DMF (20 mL) at 0° C. was added MeNHOMe·HCl (1 g, 10.3 mmol), DIEA (6 mL) and BOP (2.5 g, 5.6 mmol). The solution was stirred at 0° C. for 10 hours. DMF was evaporated by vacuum. The oily residue was dissolved in EtOAc (200 mL) and water (20 mL). The organic layer was washed with sat. NaHCO3, water (20 mL), 1 M HCl (10 mL) and sat. NaCl (2×20 mL). The organic layer was dried over MgSO4, filtered and evaporated to give a suspension. The suspension was filtered, and the solid was washed with cold EtOAc (10 mL) and dried to give Boc-Arg(Tos)-N(Me)OMe, shown above, (1.5 g, 70% yield).

Aufarbeitung

  1. customDMF was evaporated by vacuum
  2. dissolutionThe oily residue was dissolved in EtOAc (200 mL)
  3. washThe organic layer was washed with sat. NaHCO3, water (20 mL), 1 M HCl (10 mL) and sat. NaCl (2×20 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a suspension
  8. filtrationThe suspension was filtered
  9. washthe solid was washed with cold EtOAc (10 mL)
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-1269af789f834684992516fd2712e1d5
Quelldatensatz
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06133256

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