L-Lactic Acid → Onalespib Lactate

HRID 241828

Reaktionsgleichung

Reaktionsgleichung von HRID 241828
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([CH:9]([CH3:11])[CH3:10])=[CH:4][C:3]=1[C:12]([N:14]1[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([CH2:23][N:24]3[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]3)[CH:20]=2)[CH2:15]1)=[O:13].[C:31]([OH:36])(=[O:35])[C@H:32]([CH3:34])[OH:33]>C(O)C>[C:31]([OH:36])(=[O:35])[C@H:32]([CH3:34])[OH:33].[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([CH:9]([CH3:10])[CH3:11])=[CH:4][C:3]=1[C:12]([N:14]1[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([CH2:23][N:24]3[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]3)[CH:20]=2)[CH2:15]1)=[O:13]

Komponenten

4

Edukt 2

HCID 107689L-Lactic AcidHCID 11955716Onalespib

Produkt 1

HCID 46915024Onalespib LactateAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

The product of Step 12 (646 g, 1.58 mol) was dissolved in ethanol (5.17 L) and the solution filtered. A solution of L-lactic acid (142 g, 1.58 mol) dissolved in ethanol (2.59 L) was filtered and added to the solution of the filtered solution (above) and then to the mixture was added EtOAc (7.75 L). The suspension was stirred at RT for 12 h and then cooled to 5° C. for a further 2 h. The solid which had formed was removed by filtration, washed with EtOAc (2×2.58 L) and heptane (2×1.94 L) and dried to constant weight at 35° C. giving the title compound (581 g, 74% yield).

Aufarbeitung

  1. filtrationthe solution filtered
  2. filtrationwas filtered
  3. additionadded to the solution of the filtered solution (above)
  4. additionto the mixture was added EtOAc (7.75 L)
  5. temperaturecooled to 5° C. for a further 2 h
  6. customThe solid which had formed
  7. customwas removed by filtration
  8. washwashed with EtOAc (2×2.58 L) and heptane (2×1.94 L)
  9. customdried to constant weight at 35° C.

Quellen und Nachweise

ORD-Eintrag
ord-d4e4936a1e924f9fbd972bda12ce44f6
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653084B2

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