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 1592041Notes

Reaction equation

HRID 1592041 reaction equation
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]

Participants

4

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18476134Acetic acid ethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ba07a6cc5fd8420ba75126e2bb92cd2b
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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