Hydrochloric Acid → HCID 178519972, Verbindung

HRID 2169366Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2169366
[Si]([O:8][CH2:9][CH2:10][N:11]([CH2:42][CH:43]1[CH2:45][CH2:44]1)[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2([C:35]3[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=3)[CH2:34][CH2:33][CH2:32][CH2:31]2)[N:15]=1)=[O:13])(C(C)(C)C)(C)C.Cl.C(OCC)(=O)C>O1CCCC1>[CH:43]1([CH2:42][N:11]([CH2:10][CH2:9][OH:8])[C:12]([C:14]2[C:19]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]3([C:35]4[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=4)[CH2:34][CH2:33][CH2:32][CH2:31]3)[N:15]=2)=[O:13])[CH2:45][CH2:44]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 178455249HCID 178455249, Verbindung

Produkt 1

HCID 178519972HCID 178519972, VerbindungAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-benzyloxy-2-[1-(4-chlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopropylmethyl-amide (329) (580 mg, crude) in tetrahydrofuran (30 mL) was added 1N aq.HCl (6 mL) at room temperature and stirring was continued for 1 h (TLC; 100% ethyl acetate/UV/SiO2, Rf=0.2). Tetrahydrofuran was removed in vacuo and the crude mass was dissolved in ethyl acetate (50 mL) and washed with NaHCO3 solution (10 mL), water (20 mL) and brine (20 mL); The organic phase was dried and concentrated in vacuo to get a crude mass which was purified by CombiFlash using a gradient eluent mixture of ethyl acetate and hexane to get pure 5-benzyloxy-2-[1-(4-chlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid cyclopropylmethyl-(2-hydroxyethyl)-amide (330) (390 mg, 94% two steps) as an off-white sticky solid.

Aufarbeitung

  1. customTetrahydrofuran was removed in vacuo
  2. dissolutionthe crude mass was dissolved in ethyl acetate (50 mL)
  3. washwashed with NaHCO3 solution (10 mL), water (20 mL) and brine (20 mL)
  4. customThe organic phase was dried
  5. concentrationconcentrated in vacuo
  6. customto get a crude mass which
  7. customwas purified by CombiFlash
  8. additiona gradient eluent mixture of ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-cf9718e89474471bb2f393af4d4fb578
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045486B2

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