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Hydrochloric Acid → (2R)-2-(4-(2-methylpentyloxy)phenyl)-2-((S)-2-phenylpropanamido)ethyl acetate

HRID 1874620
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1874620
[C:1]([O:4][CH2:5][C@H:6]([NH2:20])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH:15]([CH3:19])[CH2:16][CH2:17][CH3:18])=[CH:9][CH:8]=1)(=[O:3])[CH3:2].Cl.[C:22]1([C@H:28]([CH3:32])[C:29](O)=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>O1CCCC1>[C:1]([O:4][CH2:5][C@@H:6]([C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH:15]([CH3:19])[CH2:16][CH2:17][CH3:18])=[CH:11][CH:12]=1)[NH:20][C:29](=[O:30])[C@H:28]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:32])(=[O:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 27246222-Phenylpropionic acid, (+)-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67085753HCID 67085753, Verbindung

Produkt 1

HCID 67086148
(2R)-2-(4-(2-methylpentyloxy)phenyl)-2-((S)-2-phenylpropanamido)ethyl acetate
Ausbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (2R)-2-amino-2-(4-(2-methylpentyloxy)phenyl)ethyl acetate.HCl (400 mg, 1.432 mmol) and (S)-2-phenylpropanoic acid (323 mg, 2.15 mmol) in tetrahydrofuran (8 mL) at 0° C. was added N,N-diisopropylethylamine (0.875 mL, 5.01 mmol) followed by HATU (817 mg, 2.15 mmol). The cooling bath was removed and the mixture was stirred at room temperature under N2 overnight. The reaction mixture was transferred to a separatory funnel containing saturated aqueous NaHCO3 solution (25 mL). The aqueous layer was extracted with ethyl acetate (3×25 mL). The combined organic layers were washed with brine (25 mL), dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography on silica gel (30%→45% ethyl acetate in hexanes; 40 g column) and dried under vacuum to afford (2R)-2-(4-(2-methylpentyloxy)phenyl)-2-((S)-2-phenylpropanamido)ethyl acetate (430 mg, 73.0% yield) as a colorless solid: 1H NMR (400 MHz, CDCl3) δ 7.22-7.37 (m, 5H), 6.95 (d, J=8.6 Hz, 2H), 6.76 (d, J=8.8 Hz, 2H), 5.87 (d, J=8.1 Hz, 1H), 5.16 (td, J=7.7, 4.5 Hz, 1H), 4.25 (dd, J=11.5, 7.4 Hz, 1H), 4.14 (dd, J=11.3, 4.5 Hz, 1H), 3.74 (dd, J=8.8, 5.8 Hz, 1H), 3.65 (dd, J=8.8, 6.8 Hz, 1H), 3.59 (q, J=7.1 Hz, 1H), 1.95 (s, 3H), 1.85-1.95 (m, 1H), 1.49 (d, J=7.3 Hz, 3H), 1.24-1.47 (m, 3H), 1.13-1.23 (m, 1H), 0.97 (d, J=6.8 Hz, 3H), 0.90 (t, J=7.3 Hz, 3H); LRMS (ESI) m/e 412.2 [(M+H)+, calcd for C25H34NO4 412.3].

Aufarbeitung

  1. customThe cooling bath was removed
  2. customThe reaction mixture was transferred to a separatory funnel
  3. additioncontaining saturated aqueous NaHCO3 solution (25 mL)
  4. extractionThe aqueous layer was extracted with ethyl acetate (3×25 mL)
  5. washThe combined organic layers were washed with brine (25 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica gel (30%→45% ethyl acetate in hexanes; 40 g column)
  10. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3635614f1ac94831be2d61a84c6ddc23
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08304577B2

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