Hydrochloric Acid → HCID 59284760, Verbindung

HRID 389855Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 389855
C[O:2][C:3]([C@H:5]1[CH2:9][C@@H:8]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@@H:7]([OH:18])[CH2:6]1)=[O:4].N1C=CN=C1.[CH3:24][C:25]([Si:28](Cl)([CH3:30])[CH3:29])([CH3:27])[CH3:26].Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C.C(O)(C)C.[OH-].[Na+].C(Cl)(Cl)Cl>[C:11]([NH:10][C@@H:8]1[CH2:9][C@H:5]([C:3]([OH:2])=[O:4])[CH2:6][C@@H:7]1[O:18][Si:28]([C:25]([CH3:27])([CH3:26])[CH3:24])([CH3:30])[CH3:29])([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Komponenten

10

Edukt 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 2734526methyl (1S,3R,4S)-3-{[(tert-butoxy)carbonyl]amino}-4-hydroxycyclopentane-1-carboxylate

Produkt 1

HCID 59284760HCID 59284760, VerbindungAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 3776IsopropanolLösungsmittelHCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

To a stirring solution of N-Boc-1(R)-amino-2(S)-hydroxy-cyclopentane-4(S)-carboxylic acid methyl ester (0.622 g, 2.40 mmol) in DCM (1.9 mL) was added imidazole (0.164 g, 2.41 mmol), DMAP (0.047 g, 0.35 mmmol) and TBSCl (0.363 g, 2.40 mmol) and the reaction was stirred at room temperature for 18 hours, followed by heating at 40° C. for 1 hour. The reaction mixture was cooled to room temperature, and was quenched with H2O (3 mL). The organic layer was separated and was concentrated to dryness to yield a residue, which was dissolved in isopropanol (6 mL) and 1M NaOH (2.9 mL), and the reaction was heated at 60° C. for 1 hour. The reaction was cooled to 0° C. and slowly acidified to pH 3 with 1M HCl (3 mL). After adding chloroform (18 mL), the organic layer was separated, dried over Na2SO4, and concentrated to dryness to yield the desired acid (0.75 g, 2.09 mmol, 87.1% yield).

Aufarbeitung

  1. temperatureby heating at 40° C. for 1 hour
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customwas quenched with H2O (3 mL)
  4. customThe organic layer was separated
  5. concentrationwas concentrated to dryness
  6. customto yield a residue, which
  7. temperatureThe reaction was cooled to 0° C.
  8. customthe organic layer was separated
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-0b24c490a7f4481e9316556dace9e370
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383596B2

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