Sodium borohydride → HCID 67348945, Verbindung

HRID 527982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 527982
[O:1]=[C:2]1[N:6]([C:7]2[CH:8]=[CH:9][C:10]3[S:15][CH2:14][C:13](=[O:16])[NH:12][C:11]=3[CH:17]=2)[CH2:5][C@@H:4]([CH2:18][CH2:19][CH2:20][NH:21][C@H:22]2[C:32]3[C:33]4[N:24]([C:25](=[O:34])[CH:26]=[N:27][C:28]=4[CH:29]=[CH:30][CH:31]=3)[CH2:23]2)[O:3]1.[BH4-].[Na+]>CO.ClCCCl>[O:1]=[C:2]1[N:6]([C:7]2[CH:8]=[CH:9][C:10]3[S:15][CH2:14][C:13](=[O:16])[NH:12][C:11]=3[CH:17]=2)[CH2:5][C@@H:4]([CH2:18][CH2:19][CH2:20][NH:21][C@H:22]2[C:32]3[C:33]4[N:24]([C:25](=[O:34])[CH2:26][NH:27][C:28]=4[CH:29]=[CH:30][CH:31]=3)[CH2:23]2)[O:3]1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 45380794HCID 45380794, Verbindung

Produkt 1

HCID 67348945HCID 67348945, VerbindungAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22134543HCID 22134543, VerbindungLösungsmittel

Versuchsvorschrift

A solution of the compound of Example 48 (33 mg) in MeOH/DCE (5 mL; 4:1) was treated with NaBH4 (3 mg) for 30 min then quenched with 1M HCl (1 mL) and partitioned between DCM and an aq. NH4OH solution. The org. layer was washed with water and brine, dried over MgSO4 and purified by CC (EA/MeOH 19:1 to 9:1 containing 1% NH4OH) affording a colourless solid (26 mg; 78% yield).

Aufarbeitung

  1. customthen quenched with 1M HCl (1 mL)
  2. custompartitioned between DCM
  3. washlayer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. custompurified by CC (EA/MeOH 19:1 to 9:1 containing 1% NH4OH)
  6. customaffording a colourless solid (26 mg; 78% yield)

Quellen und Nachweise

ORD-Eintrag
ord-e319c8107bad4da9832d6a0f287dc789
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346804B2

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