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Benzyl Alcohol → Benzyl 1-{{{[2(R)-Hydroxycyclopent-1(R)-yl]oxy}carbonyl}aminomethyl}-1-Cyclohexane Acetate

HRID 252305
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 252305
[OH:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[O:7][C:8]([NH:10][CH2:11][C:12]1([CH2:18][C:19]([OH:21])=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:9].C1(N=C=NC2CCCCC2)CCCCC1.[CH2:37](O)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>CN(C1C=CN=CC=1)C.ClCCl>[OH:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[O:7][C:8]([NH:10][CH2:11][C:12]1([CH2:18][C:19]([O:21][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:9]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 865905641-{{{[2(R)-Hydroxycyclopent-1(R)-yl]oxy}carbonyl}aminomethyl}-1-Cyclohexane Acetic Acid

Produkt 1

HCID 86590565Benzyl 1-{{{[2(R)-Hydroxycyclopent-1(R)-yl]oxy}carbonyl}aminomethyl}-1-Cyclohexane AcetateAusbeute 78,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14284
4-(Dimethylamino)pyridine
Katalysator
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of compound (49) (0.5 g, 1.67 mmol), 1,3-dicyclohexylcarbodiimide (1.0 g, 5.0 mmol) and DMAP (19 mg, 0.16 mmol) in dichloromethane (100 mL) at room temperature under nitrogen atmosphere was added benzyl alcohol (1.1 mL, 10 mmol). The reaction mixture was stirred at room temperature for 15 h (monitored by tlc and LC/MS), then filtered, and the white solid was washed with dichloromethane (2×15 mL). The combined filtrates were washed with water (2×25 mL), dried over Na2SO4 and concentrated in vacuo. The crude product was purified using flash chromatography on silica gel using hexane/ethyl acetate (2:1) as eluant to provide 0.51 g (78%) of compound (50) as a colorless liquid. 1H NMR (400 MHz, CDCl3): δ 1.36-1.75 (14H, m); 1.99-2.10 (2H, m); 2.35 (2H, s); 3.17 (2H, d, J=6.8 Hz); 4.05 (1H, m); 4.65 (1H, m); 5.12 (2H, s); 5.34 (1H, t, J=6.8 Hz); 7.36 (5H, m). MS (ESI): m/z=390.22 (M+H+).

Aufarbeitung

  1. filtrationfiltered
  2. washthe white solid was washed with dichloromethane (2×15 mL)
  3. washThe combined filtrates were washed with water (2×25 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified

Quellen und Nachweise

ORD-Eintrag
ord-e6452867adca4e5ab6360e15f50ddcce
Quelldatensatz
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07868041B2

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