1-tert-Butyl 2-methyl (2S)-4-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)pyrrolidine-1,2-dicarboxylate → Methyl 4-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-L-prolinate

HRID 2233945Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2233945
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15]([CH:18]2[CH2:22][N:21](C(OC(C)(C)C)=O)[C@H:20]([C:30]([O:32][CH3:33])=[O:31])[CH2:19]2)[CH2:14][CH2:13]1)=[O:10]>Cl.O1CCOCC1>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:13][CH2:14][N:15]([CH:18]2[CH2:22][NH:21][C@H:20]([C:30]([O:32][CH3:33])=[O:31])[CH2:19]2)[CH2:16][CH2:17]1)=[O:10]

Komponenten

4

Edukt 1

HCID 866082951-tert-Butyl 2-methyl (2S)-4-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)pyrrolidine-1,2-dicarboxylate

Produkt 1

HCID 68579931Methyl 4-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-L-prolinateAusbeute 101,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

1-tert-Butyl 2-methyl (2S)-4-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)pyrrolidine-1,2-dicarboxylate (Example 51, 0.16 g, 0.32 mM) was stirred in 4 N hydrogen chloride in dioxane (4.0 ml) at room temperature for twenty minutes. The orange mixture was concentrated then dissolved in a small amount of MeOH/DCM, diluted with DCM, and washed with sodium bicarbonate. The organic layer was dried over MgSO4, filtered and concentrated to give an orange solid (0.130 g).

Aufarbeitung

  1. concentrationThe orange mixture was concentrated
  2. dissolutionthen dissolved in a small amount of MeOH/DCM
  3. additiondiluted with DCM
  4. washwashed with sodium bicarbonate
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-043638ce1e214320b6f47d2bcfa07f63
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709503B2

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