HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → (2-Hydroxycarbamoyl-1-(4-methoxybenzene sulfonyl)-2,3,4,7-tetrahydro-1H-azepine-3-yl)-carbamic acid benzyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 3-Benzyloxycarbonylamino-1-(4-methoxy-benzene sulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2-carboxylic Acid | HCID 15550527 | — |
| Reactant | t-Butyldimethylsilylhydroxylamine | HCID 17809443 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (2-Hydroxycarbamoyl-1-(4-methoxybenzene sulfonyl)-2,3,4,7-tetrahydro-1H-azepine-3-yl)-carbamic acid benzyl ester | HCID 54472606 | — |
Reaction Steps
3-Benzyloxycarbonylamino-1-(4-methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2-carboxylic acid (21 mg, 0.043 mmol) is dissolved in dry Dimethylformamide (DMF) and cooled to -20° C. tert-Butyldimethylsilylhydroxyl amine (7 mg, 0.05 mmol), Hunigs Base (9.8 μl, 0.05 mmol) and O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate (HATU) (18 mg, 0.05 mmol) are added. The reaction solution is stirred for 1 h and then allowed to warm to room temp. The solvent is evaporated. The residue is purified by flash-chromatography, Dichloromethane/Methanol (9:1), to afford the desired hydroxamide: Cal. 476.5, Found (MH)+ 476.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06107291 |
| Source dataset | uspto-grants-2000_08 |
| ORD ID | ord-1ae1e808c2df42f19b4c68eacb5bf125 |
| Source note | uspto-grants-2000_08 |