Ammonia → HCID 19920940, compound
Reaction equation
[CH2:1]([N:5]([CH2:31][CH2:32][SH:33])[CH2:6][CH2:7][CH2:8][N:9]([CH2:20][CH2:21][CH2:22][N:23]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:24][CH2:25][SH:26])S(C1C=CC(C)=CC=1)(=O)=O)[CH2:2][CH2:3][CH3:4].N.[Na].C(OCC)C>O1CCCC1.O.C(O)C>[CH2:1]([N:5]([CH2:6][CH2:7][CH2:8][NH:9][CH2:20][CH2:21][CH2:22][N:23]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:24][CH2:25][SH:26])[CH2:31][CH2:32][SH:33])[CH2:2][CH2:3][CH3:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -78 °C
Procedure
Dissolve N,N-bis-{3-[butyl-(2-mercapto-ethyl)-amino]-propyl}-4-methyl-benzenesulfonamide (10 mmol) prepared in Scheme IX, step B in dry tetrahydrofuran (50 mL) and cool the solution to -78° C. Add excess dry ammonia followed by excess sodium. Stir the reaction for 4 hours and then warm to room temperature overnight. Add diethyl ether (100 mL) followed by cautious addition of ethanol (30 mL). After stirring for 30 minutes cautiously add water dropwise (5 mL) and then concentrate the reaction under vacuum. Extract the residue with diethyl ether (100 mL) and chloroform (100 mL). Combine the organic extracts, dry over anhydrous sodium sulfate, filter and concentrate under vacuum. Purify the residue by flash chromatography (silica gel, methanol/methylene chloride) to provide the title compound.
Workup
- customthe reaction for 4 hours
- temperaturewarm to room temperature overnight
- concentrationconcentrate
- customthe reaction under vacuum
- extractionExtract the residue with diethyl ether (100 mL) and chloroform (100 mL)
- dry with materialCombine the organic extracts, dry over anhydrous sodium sulfate
- filtrationfilter
- concentrationconcentrate under vacuum
- customPurify the residue by flash chromatography (silica gel, methanol/methylene chloride)
Sources & evidence
- ORD record
- ord-ab4334c4d301438caa5cd144aff131f3
- Source dataset
- uspto-grants-1995_07
- Patent number
- US05434145
Reaction notes
Loading…