3-[3-benzyloxy-4-(1,1,4-trioxo-[1,2,5]thiadiazolidin-2-yl)-benzyl]-3,4-dihydro-1H-benzo[1,4]diazepine-2,5-dione → 3-[3-hydroxy-4-(1,1,4-trioxo-[1,2,5]thiadiazolidin-2-yl)-benzyl]-3,4-dihydro-1H-benzo[1,4]diazepine-2,5-dione

HRID 1592041Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1592041
C([O:8][C:9]1[CH:10]=[C:11]([CH:26]=[CH:27][C:28]=1[N:29]1[CH2:33][C:32](=[O:34])[NH:31][S:30]1(=[O:36])=[O:35])[CH2:12][CH:13]1[NH:19][C:18](=[O:20])[C:17]2[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=2[NH:15][C:14]1=[O:25])C1C=CC=CC=1>C(O)C.C(O)(=O)C.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH:26]=[CH:27][C:28]=1[N:29]1[CH2:33][C:32](=[O:34])[NH:31][S:30]1(=[O:36])=[O:35])[CH2:12][CH:13]1[NH:19][C:18](=[O:20])[C:17]2[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=2[NH:15][C:14]1=[O:25]

Komponenten

4

Edukt 1

HCID 671383483-[3-benzyloxy-4-(1,1,4-trioxo-[1,2,5]thiadiazolidin-2-yl)-benzyl]-3,4-dihydro-1H-benzo[1,4]diazepine-2,5-dione

Produkt 1

HCID 589974043-[3-hydroxy-4-(1,1,4-trioxo-[1,2,5]thiadiazolidin-2-yl)-benzyl]-3,4-dihydro-1H-benzo[1,4]diazepine-2,5-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 18476134Acetic acid ethanolLösungsmittel

Versuchsvorschrift

A solution of 3-[3-benzyloxy-4-(1,1,4-trioxo-[1,2,5]thiadiazolidin-2-yl)-benzyl]-3,4-dihydro-1H-benzo[1,4]diazepine-2,5-dione (452 mg, 0.89 mmol) in ethanol-acetic acid (2:1, 12 mL) is hydrogenated over 10% palladium on charcoal catalyst (106 mg) at 50 psi for 24 h. The catalyst is filtered and the filtrate is evaporated to dryness. The residue is purified by LC-MS, on a Gilson-Micromass instrument using a Phenominex Luna, 5μ, 60×21.2 mm, C-8 column, a gradient of 5% to 100% over 8 min with solvent A (water, 0.1% trifluoroacetic acid) and B (MeCN, 0.1% trifluoroacetic acid) with flow rate 20 mL/min, UV detector at 215 nm and cone voltage setting at 30 V. The purification is conducted with several runs with 50 mg of crude material being used in each run (approximately 16 runs). Pure fractions are pooled and evaporated to dryness, the residue is dissolved in water-MeCN and the solution is filtered and the filtrate is concentrated to give 3-[3-hydroxy-4-(1,1,4-trioxo-[1,2,5]thiadiazolidin-2-yl)-benzyl]-3,4-dihydro-1H-benzo[1,4]diazepine-2,5-dione as an amorphous solid: mp=180° C.; [M+1]+=417.

Aufarbeitung

  1. filtrationThe catalyst is filtered
  2. customthe filtrate is evaporated to dryness
  3. customThe residue is purified by LC-MS, on a Gilson-Micromass instrument
  4. customThe purification
  5. customevaporated to dryness
  6. dissolutionthe residue is dissolved in water-MeCN
  7. filtrationthe solution is filtered
  8. concentrationthe filtrate is concentrated

Quellen und Nachweise

ORD-Eintrag
ord-ba07a6cc5fd8420ba75126e2bb92cd2b
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07291635B2

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