Thioglycolic Acid → 8-Carboxymethylthio-5'-azido-5'-deoxyadenosine

HRID 1422557

Reaktionsgleichung

Reaktionsgleichung von HRID 1422557
[C:1]([OH:5])(=[O:4])[CH2:2][SH:3].[H-].[Na+].Br[C:9]1[N:10]([C:22]2[N:23]=[CH:24][N:25]=[C:26]([NH2:29])[C:27]=2[N:28]=1)[C@@H:11]1[O:21][C@H:16]([CH2:17][N:18]=[N+:19]=[N-:20])[C@@H:14]([OH:15])[C@H:12]1[OH:13].C([O-])(=O)CS>CN(C=O)C>[C:1]([CH2:2][S:3][C:9]1[N:10]([C:22]2[N:23]=[CH:24][N:25]=[C:26]([NH2:29])[C:27]=2[N:28]=1)[C@@H:11]1[O:21][C@H:16]([CH2:17][N:18]=[N+:19]=[N-:20])[C@@H:14]([OH:15])[C@H:12]1[OH:13])([OH:5])=[O:4]

Komponenten

6

Edukt 4

HCID 1133Thioglycolic AcidHCID 24758Sodium hydrideHCID 5086465Acetic acid, mercapto-, ion(1-)HCID 867043935'-Azido-8-Bromo-5'-Deoxyadenosine

Produkt 1

HCID 867043928-Carboxymethylthio-5'-azido-5'-deoxyadenosineAusbeute 56,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

A solution of thioglycolic acid (0.2 mmol) and NaH (0.4 mmol, 60% in oil) in anhydrous DMF (2 mL) was stirred for 10 min, then 8-bromo-5′-azido-5′-deoxyadenosine (8) (50 mg, 0.13 mmol) in DMF (1 mL) was added at 0° C. After 8 h at room temperature, more thioglycolate (0.2 mmol) in DMF was added. After stirring overnight, the reaction mixture was concentrated to dryness and the residue purified by reverse phase HPLC (10-30% ACN in TEAA over 20 min) to give 10 (28 mg, 56%); UV λmax 279 nm; HRMS (ESI-TOF) m/z calcd for C12H14N8O5S (M+H) 383.0886; found 383.0890.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated to dryness
  2. customthe residue purified by reverse phase HPLC (10-30% ACN in TEAA over 20 min)

Quellen und Nachweise

ORD-Eintrag
ord-0782ed974504424b8371e728d7cd904d
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927520B2

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