N-Hydroxyphthalimide → 7-[3,5-Dihydroxy-2-(3-hydroxy-5-phenyl-pent-1-enyl)-cyclopentyl]-5-heptenoic acid 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester

HRID 591123Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 591123
CCN[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].[OH:31][N:32]1[C:36](=[O:37])[C:35]2=[CH:38][CH:39]=[CH:40][CH:41]=[C:34]2[C:33]1=[O:42].C(N=C=NC(C)C)(C)C.OS([O-])(=O)=O.[Na+]>C1COCC1.COC(C)(C)C>[O:37]=[C:36]1[C:35]2[C:34](=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:33](=[O:42])[N:32]1[O:31][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH:12]1[CH:13]([OH:30])[CH2:14][CH:15]([OH:29])[CH:16]1[CH:17]=[CH:18][CH:19]([OH:28])[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

7

Edukt 4

HCID 10665N-HydroxyphthalimideHCID 12734DiisopropylcarbodiimideHCID 516919Sodium BisulfateHCID 5311027Bimatoprost

Produkt 1

HCID 867188447-[3,5-Dihydroxy-2-(3-hydroxy-5-phenyl-pent-1-enyl)-cyclopentyl]-5-heptenoic acid 1,3-dioxo-1,3-dihydro-isoindol-2-yl esterAusbeute 58,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

2 g of bimatoprost acid is dissolved in 20 ml of THF and to this solution are added at room temperature 1 g of N-hydroxy-phtalimide and 1 ml of N,N′-diisopropylcarbodiimide. The reaction mixture is stirred for 2 hours and then poured onto they mixture of 1N NaHSO4 solution and tert-butyl methyl ether (TBME). The phases are separated, the organic phase is washed with 1N NaHCO3 solution and the aqueous-alkaline phase is extracted with TBME. The united organic phase is dried over Na2SO4, filtered and evaporated. The residue is crystallized from hexane:acetone mixture to obtain 1.5 g white crystalline material.

Aufarbeitung

  1. customThe phases are separated
  2. washthe organic phase is washed with 1N NaHCO3 solution
  3. extractionthe aqueous-alkaline phase is extracted with TBME
  4. dry with materialThe united organic phase is dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is crystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-ad00af67107b4dd7aad85ac24db0a68e
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238621B2

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