Methanol → HCID 22672527, Verbindung

HRID 47969

Reaktionsgleichung

Reaktionsgleichung von HRID 47969
[CH3:1][C:2]([CH3:26])([CH3:25])[C:3]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]=[C:11]3[C:16]([O:17][C:18]=2[CH:19]=1)=[CH:15][C:14](=[O:20])[C:13]([CH2:21][CH2:22][CH2:23][OH:24])=[CH:12]3)=[O:4].C(N(CC)CC)C.[CH:34]([N:37]([CH:45]([CH3:47])[CH3:46])[P:38](Cl)[O:39][CH2:40][CH2:41][C:42]#[N:43])([CH3:36])[CH3:35].CO>C(Cl)Cl.CCOCC.CCCCCC>[CH3:1][C:2]([CH3:26])([CH3:25])[C:3]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]=[C:11]3[C:16]([O:17][C:18]=2[CH:19]=1)=[CH:15][C:14](=[O:20])[C:13]([CH2:21][CH2:22][CH2:23][O:24][P:38]([N:37]([CH:45]([CH3:47])[CH3:46])[CH:34]([CH3:35])[CH3:36])[O:39][CH2:40][CH2:41][C:42]#[N:43])=[CH:12]3)=[O:4]

Komponenten

8

Edukt 4

HCID 887MethanolHCID 8471TriethylamineHCID 27348442-Cyanoethyl N,N-diisopropylchlorophosphoramiditeHCID 22672525HCID 22672525, Verbindung

Produkt 1

HCID 22672527HCID 22672527, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

36b (0.38 g, 1.1 mmol) was dissolved in 6 mL of anhydrous CH2Cl2. Triethylamine (1.5 mL) was added followed by 2-cyanoethyl diisopropylchlorophosphoramidite (0.29 mL, 1.3 mmol). The solution was kept at room temperature for 30 min, MeOH (0.1 mL) was added and the reaction was concentrated under vacuum. The residue obtained was partitioned between ethyl acetate and NaHCO3. The organic phase was washed with saturated NaCl, dried over Na2SO4 and concentrated to afford the crude amidite. It was dissolved in 2 mL of ether and added dropwise to ˜50 mL of hexane. The resultant orange solid was collected by filtration, washed with hexane and dried. The yield was 0.4 g.

Aufarbeitung

  1. concentrationthe reaction was concentrated under vacuum
  2. customThe residue obtained
  3. customwas partitioned between ethyl acetate and NaHCO3
  4. washThe organic phase was washed with saturated NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto afford the crude amidite
  8. filtrationThe resultant orange solid was collected by filtration
  9. washwashed with hexane
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-12f83a610c1f470193d59c21eab882af
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699975B2

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