Triethylamine → tert-butyl 4-[(2S)-3-benzyloxycarbonylamino-2-hydroxy-propyl]piperazine-1-carboxylate

HRID 2364711Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2364711
[NH2:1][CH2:2][C@H:3]([OH:18])[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.C(N(CC)CC)C.[C:26](Cl)([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27].C(=O)(O)[O-].[Na+]>ClCCl>[CH2:29]([O:28][C:26]([NH:1][CH2:2][C@H:3]([OH:18])[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[CH2:7][CH2:6]1)=[O:27])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 7144880tert-butyl 4-[(2S)-3-amino-2-hydroxy-propyl]piperazine-1-carboxylate

Produkt 1

HCID 68107178tert-butyl 4-[(2S)-3-benzyloxycarbonylamino-2-hydroxy-propyl]piperazine-1-carboxylateAusbeute 76,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Tert-butyl 4-[(2S)-3-amino-2-hydroxy-propyl]piperazine-1-carboxylate 7c (1.24 g, 4.80 mmol) was dissolved in 60 mL of dichloromethane followed by the addition of triethylamine (970 mg, 9.60 mmol) and carbobenzoxy chloride (0.90 g, 5.28 mmol). The reaction solution was stirred for 2 hours. The resulting solution was added with 50 mL of saturated sodium bicarbonate solution and extracted with dichloromethane (50 mL×3). The combined organic phase was washed with saturated sodium chloride solution (50 mL×3), then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound tert-butyl 4-[(2S)-3-benzyloxycarbonylamino-2-hydroxy-propyl]piperazine-1-carboxylate 21a (1.45 g, yield: 76.0%) as a colorless oil.

Aufarbeitung

  1. extractionextracted with dichloromethane (50 mL×3)
  2. washThe combined organic phase was washed with saturated sodium chloride solution (50 mL×3)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5c2c1d6fb84f47d79356f6c48328a7cd
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691822B2

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