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Lithium Chloride → Tert-butyl 2-(3-(3-chloro-4-(2-hydroxyethyl)phenyl)ureido)cyclohexylcarbamate

HRID 1023860
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1023860
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[NH:15][C:16](=[O:31])[NH:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25](OCC)=[O:26])=[C:20]([Cl:30])[CH:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].[Li+].[Cl-]>C1COCC1.CCO>[Cl:30][C:20]1[CH:19]=[C:18]([NH:17][C:16](=[O:31])[NH:15][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH:9]2[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH:23]=[CH:22][C:21]=1[CH2:24][CH2:25][OH:26]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 67204990Ethyl 2-(4-(3-(2-(tert-butoxycarbonylamino)cyclohexyl)ureido)-2-chlorophenyl)acetate

Produkt 1

HCID 67206716Tert-butyl 2-(3-(3-chloro-4-(2-hydroxyethyl)phenyl)ureido)cyclohexylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21873804
Tetrahydrofuran ethanol
Lösungsmittel

Versuchsvorschrift

To a solution of ethyl 2-(4-(3-(2-(tert-butoxycarbonylamino)cyclohexyl)ureido)-2-chlorophenyl)acetate (452 mg, 0.996 mmol) in a mixture of THF:EtOH (1:2, 12 mL) at room temperature, was added NaBH4 (124 mg, 3.29 mmol) and LiCl (139 mg, 3.29 mmol). The reaction mixture was stirred overnite. The solvents were distilled off and the crude was diluted with saturated aqueous NH4Cl (20 mL), the product was extracted with ethyl acetate (2×20 mL). The combined organic extracts were dried over Na2SO4 and the solvent distilled off under reduced pressure. The crude product was purified by flash column chromatography to separate cis 964 mg, 0.155 mmol) and trans (83 mg, 0.201 mmol) diastereomers. These alcohols were converted into tosylates using general procedure for the preparation of tosylates. 1H NMR (cis): 1.23-1.26 (m, 3H), 1.36 (s, 9H), 1.70-1.74 (m, 2H), 1.99-2.06 (m, 2H), 2.41-2.43 (m, 1H), 2.92 (t, 2H, J=6.4 Hz), 3.25-3.29 (m, 1H), 3.51-3.54 (m, 1H), 3.83-3.86 (m, 2H), 5.03 (d, 1H, J=8.8 Hz), 5.62 (d, 1H, J=8.4 Hz), 7.04 (d, 1H, J=8.4 Hz), 7.09 (d, 1H, J=8 Hz), 7.32 (s, 2H). 1H NMR (trans): 1.26-1.29 (m, 1H), 1.37-1.42 (m, 12H), 1.69-1.72 (m, 2H), 1.97 (s, 1H), 2.53-2.55 (m, 1H), 2.85 (t, 2H, J=6.4 Hz), 3.75-3.77 (m, 3H), 3.97-3.99 (m, 1H), 5.15 (br s, 1H), 5.86 (br s, 1H), 6.98-7.05 (m, 2H), 7.30 (s, 1H), 7.41 (s, 2H).

Aufarbeitung

  1. distillationThe solvents were distilled off
  2. additionthe crude was diluted with saturated aqueous NH4Cl (20 mL)
  3. extractionthe product was extracted with ethyl acetate (2×20 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. distillationthe solvent distilled off under reduced pressure
  6. customThe crude product was purified by flash column chromatography
  7. customto separate cis 964 mg, 0.155 mmol) and trans (83 mg, 0.201 mmol) diastereomers
  8. customThese alcohols were converted into tosylates using general procedure for the preparation of tosylates

Quellen und Nachweise

ORD-Eintrag
ord-2cf8acc454574a6f8fa4b384e0ae93bf
Quelldatensatz
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08722720B2

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