Chlorotrimethylsilane → HCID 15137392, compound

HRID 981856Notes

Reaction equation

HRID 981856 reaction equation
C(N(CC)C(C)C)(C)C.[Si](Cl)(C)(C)C.[NH2:15][CH2:16][CH:17]([SH:20])[CH2:18][CH3:19].Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1)=[O:23]>CC#N>[N+:32]([C:29]1[CH:28]=[CH:27][C:26]([CH2:25][O:24][C:22]([NH:15][CH2:16][CH:17]([SH:20])[CH2:18][CH3:19])=[O:23])=[CH:31][CH:30]=1)([O-:34])=[O:33]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 782054-Nitrobenzyl chloroformateHCID 81531Diisopropylethylamine2×HCID 1658861-Aminobutane-2-thiol

Product 1

HCID 15137392HCID 15137392, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

N,N-Diisopropylethylamine (8.50 ml, 0.0488 mol) and Me3SiCl (3.50 ml, 0.0239 mol) were added to an ice-cold, stirring solution of 1-amino-2-butanethiol (3.00 g, 0.0212 mol) in MeCN (16.0 ml). The solution was stirred 10 minutes at 0°, then treated with more N,N-diisopropylethylamine (3.70 ml, 0.0212 mol) and with a solution of p-nitrobenzyl chloroformate (4.57 g, 0.0212 mol) in MeCN (5.0 ml). The resulting mixture was stirred for 30 minutes at 0° and 90 minutes at room temperature. The mixture was poured into ice-water (50 ml) and extracted with EtOAc (75 ml). The organic phase was separated, washed with 1.25N HCl, 5% NaHCO3, and brine, dried with MgSO4, filtered and evaporated under vacuum to an oil (5.79 g).

Workup

  1. stirringThe resulting mixture was stirred for 30 minutes at 0° and 90 minutes at room temperature
  2. extractionextracted with EtOAc (75 ml)
  3. customThe organic phase was separated
  4. washwashed with 1.25N HCl, 5% NaHCO3, and brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customevaporated under vacuum to an oil (5.79 g)

Sources & evidence

ORD record
ord-ef572269504840e79d7ecb1be588b54f
Source dataset
uspto-grants-1991_02
Patent number
US04992542

Reaction notes

Loading…