Formaldehyde → HCID 77078276, Verbindung

HRID 446184Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 446184
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C@H:11]([OH:24])[CH2:12][C@@H:13]([NH:17][S@:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])[CH:14]([CH3:16])[CH3:15])[S:9][CH:10]=1)=[O:5])[CH3:2].[CH2:25]=O>C1(C)C=CC=CC=1>[CH3:2][CH2:1][O:3][C:4]([C:6]1[N:7]=[C:8]([C@@H:11]2[O:24][CH2:25][N:17]([S:18]([C:20]([CH3:21])([CH3:22])[CH3:23])=[O:19])[CH:13]([CH:14]([CH3:15])[CH3:16])[CH2:12]2)[S:9][CH:10]=1)=[O:5]

Komponenten

4

Edukt 2

HCID 712FormaldehydeHCID 24906124ethyl 2-((1R,3R)-3-(N-sulfinyl)amino-1-hydroxy-4-methylpentyl)thiazole-4-carboxylate

Produkt 1

HCID 77078276HCID 77078276, VerbindungAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A 0.1 M solution of N-sulfinyl amino alcohol 32 (0.575 g, 1.53 mmol) in toluene (15.3 mL) with paraformaldehyde (0.917 g, 30.5 mmol) was heated in a sealed vessel at 70° C. with stirring for 50 h. After cooling to rt, the mixture was filtered through Celite, washing the filter cake thoroughly with toluene. The solution was concentrated and purified via HPFC (88:12 to 30:70 CH2Cl2:EtOAc) to afford 0.518 g of tetrahydrooxazine 33 (87%) as a foamy yellow solid. [α]25D=+108.4 (c=1.0, CHCl3). IR (film): 1011, 1076, 1087, 1163, 1195, 1474, 1729, 2957, 2979 cm−1. 1H NMR (500 MHz, CDCl3): δ 1.01 (d, 3H, J=6.8 Hz), 1.02 (d, 3H, J=6.8 Hz), 1.17 (s, 9H), 1.35 (t, 3H, J=7.1 Hz), 2.08-2.16 (m, 1H), 2.28-2.40 (m, 1H), 2.31 (d, 1H, J=14.3 Hz), 3.02 (dd, 1H, J=4.7, 10.1 Hz), 4.37 (q, 2H, J=7.1 Hz), 4.72 (d, 1H, J=11.6 Hz), 5.14 (d, 1H, J=11.6 Hz), 5.20 (dd, 1H, J=2.5, 11.5 Hz), 8.11 (s, 1H). 13C NMR (125 MHz, CDCl3): δ 14.3, 20.5, 20.7, 22.8, 27.5, 32.6, 59.2, 61.3, 62.7, 71.4, 71.6, 127.8, 146.5, 161.3, 173.3. HRMS (FAB) calcd. for C17H29N2O4S2 (M+H): 389.1569. Found 389.1566.

Aufarbeitung

  1. filtrationthe mixture was filtered through Celite
  2. washwashing the filter cake thoroughly with toluene
  3. concentrationThe solution was concentrated
  4. custompurified via HPFC (88:12 to 30:70 CH2Cl2:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-5d0224d951c94dc2bcd6a3e6d10d5b5b
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476451B2

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