Triethylamine → HCID 52872884, compound

HRID 1183083Notes

Reaction equation

HRID 1183083 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].[NH2:14][CH2:15][CH2:16][N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21].C(N(CC)CC)C>ClCCl.O>[CH3:25][N:17]([CH2:16][CH2:15][NH:14][S:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 2756424N-Boc-N-methylethylenediamine

Product 1

HCID 52872884HCID 52872884, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

2-Nitrobenzenesulfonyl chloride (4.9 g, 22 mmol) was added to a dichloromethane solution (100 ml) of tert-butyl (2-aminoethyl)methylcarbamate (3.5 g, 20 mmol) and triethylamine (3.3 ml, 24 mmol) at 0° C., and stirred at room temperature overnight. Water was added to the reaction mixture, and extraction with dichloromethane was performed. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:2→2:3). The purified product was concentrated under reduced pressure to thereby obtain 5.06 g (yield: 70%) of tert-butyl methyl-[2-(2-nitrobenzenesulfonylamino)ethyl]carbamate as a yellow oil.

Workup

  1. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:2→2:3)
  4. concentrationThe purified product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1b0ceb853cfb43e08b09635777fc9d77
Source dataset
uspto-grants-2014_03
Patent number
US08664217B2

Reaction notes

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