Hydrochloric Acid → HCID 25099089, Verbindung

HRID 1749299

Reaktionsgleichung

Reaktionsgleichung von HRID 1749299
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:35])[C:15](=[O:34])[CH2:16][O:17][C:18]2[N:23]=[C:22]([CH3:24])[C:21]([NH:25]C(=O)OC(C)(C)C)=[C:20]([CH3:33])[N:19]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(NC1C(C)=NC(OCC(O)=O)=NC=1C)=O)(C)(C)C.Cl>C(Cl)(Cl)Cl>[NH2:25][C:21]1[C:22]([CH3:24])=[N:23][C:18]([O:17][CH2:16][C:15]([N:14]([CH:11]2[CH2:12][CH2:13][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9][CH2:10]2)[CH3:35])=[O:34])=[N:19][C:20]=1[CH3:33]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 59336118HCID 59336118, VerbindungHCID 593361682-(5-(Tert-butoxycarbonylamino)-4,6-dimethylpyrimidine-2-yloxy)acetic acid

Produkt 1

HCID 25099089HCID 25099089, VerbindungAusbeute 103,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Compound 30 (calculated assuming that Compound 9 in the previous process was 74.74 g and the yield of amidation was 80%) was dissolved in chloroform (140 mL). The solution was added to a 6N aqueous HCl solution (530 mL) at room temperature (20 to 30° C.). The equipment used to add compound 30 was thoroughly washed with chloroform (240 mL) and was then stirred at room temperature (20 to 30° C.) for 2.5 hours. After the chloroform layer was separated, chloroform (300 mL) was added to the aqueous layer. While ice (740.7 g in total) was added as necessary, a 4N aqueous sodium hydroxide solution (805 mL) was added portionwise. An additional amount of 4N aqueous sodium hydroxide solution (25 mL to adjust the pH of the aqueous layer to 8.5) was added, followed by the addition of chloroform (80 mL), and separation was performed. After the chloroform layer was separated, chloroform (200 mL) was added to the aqueous layer and separation was performed again. The chloroform layer collected in the two extraction processes was dried over magnesium sulfate and suction-filtered. The filtrate was then evaporated under reduced pressure to give 100.15 g (103.9% yield, in 2 steps) of the crude desired product as a pale yellow solid.

Aufarbeitung

  1. washwas thoroughly washed with chloroform (240 mL)
  2. customAfter the chloroform layer was separated
  3. additionchloroform (300 mL) was added to the aqueous layer
  4. additionWhile ice (740.7 g in total) was added as necessary, a 4N aqueous sodium hydroxide solution (805 mL)
  5. additionwas added portionwise
  6. additionwas added
  7. additionfollowed by the addition of chloroform (80 mL), and separation
  8. customAfter the chloroform layer was separated
  9. additionchloroform (200 mL) was added to the aqueous layer and separation
  10. customThe chloroform layer collected in the two extraction processes
  11. dry with materialwas dried over magnesium sulfate
  12. filtrationsuction-filtered
  13. customThe filtrate was then evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5e5ac99fec88463b9531981f73a4b3ac
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156817B2

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