Pyridine → 4-Chlorobutyl (1S,2E)-3-{(1R,2R,3S,5R)-2-[(2Z)-7-(Ethylamino)-7-oxohept-2-en-1-yl]-3,5-dihydroxycyclopentyl}-1-(2-phenylethyl)prop-2-en-1-yl Carbonate

HRID 422893Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 422893
[CH3:1][CH2:2][NH:3][C:4]([CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][C@@H:12]1[C@@H:16](/[CH:17]=[CH:18]/[C@@H:19]([OH:28])[CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C@H:15]([OH:29])[CH2:14][C@@H:13]1[OH:30])=[O:5].B([O-])[O-].N1C=CC=CC=1.Cl[C:41]([O:43][CH2:44][CH2:45][CH2:46][CH2:47][Cl:48])=[O:42]>C1COCC1.CN(C1C=CN=CC=1)C>[C:41](=[O:42])([O:28][C@@H:19]([CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)/[CH:18]=[CH:17]/[C@H:16]1[C@H:15]([OH:29])[CH2:14][C@H:13]([OH:30])[C@@H:12]1[CH2:11]/[CH:10]=[CH:9]\[CH2:8][CH2:7][CH2:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[O:43][CH2:44][CH2:45][CH2:46][CH2:47][Cl:48]

Komponenten

6

Edukt 3

HCID 1049Pyridine2×HCID 27333284-Chlorobutyl carbonochloridate2×HCID 178465099HCID 178465099, Verbindung

Produkt 1

HCID 582316334-Chlorobutyl (1S,2E)-3-{(1R,2R,3S,5R)-2-[(2Z)-7-(Ethylamino)-7-oxohept-2-en-1-yl]-3,5-dihydroxycyclopentyl}-1-(2-phenylethyl)prop-2-en-1-yl CarbonateAusbeute 134 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of bimatoprost boronate b-1 (529 mg, 1.10 mmol) in THF was added DMAP (6.9 mg, 0.055 mmol). The solution was cooled to 0° C. and successively slowly added pyridine (0.22 mL, 2.75 mmol) and 4-chlorobutyl chloroformate (0.375 mL, 2.75 mmol). Allowed to stir at ambient temperature over 2 days. Added more pyridine (89 uL, 1.11 mmol) and 4-chlorobutyl chloroformate (150 uL, 1.10 mmol) and stirred for another 24 h. The resultant mixture was concentrated under reduced pressure, residue partitioned with ethyl acetate and water. Washed organic layer with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to provide 808 mg (134%) of a crude oil, which was used without further purification.

Aufarbeitung

  1. stirringstirred for another 24 h
  2. concentrationThe resultant mixture was concentrated under reduced pressure, residue
  3. custompartitioned with ethyl acetate and water
  4. dry with materialWashed organic layer with brine, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-140901632d314fde8f47f5142f679081
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101658B2

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