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 1592041ノート

反応式

HRID 1592041 の反応式
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]

参加物

4

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 18476134Acetic acid ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ba07a6cc5fd8420ba75126e2bb92cd2b
出典データセット
uspto-grants-2007_11
特許番号
US07291635B2

反応ノート

読み込み中…