Triethylamine → HCID 58080257, compound

HRID 879966Notes

Reaction equation

HRID 879966 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH2:15])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN(CC)CC.[O:23]([C:30]1[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CC#N>[O:23]([C:30]1[CH:35]=[CH:34][C:33]([S:36]([NH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])(=[O:38])=[O:37])=[CH:32][CH:31]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2733170N-BOC-1,6-diaminohexaneHCID 27947564-Phenoxybenzene-1-sulfonyl chloride

Product 1

HCID 58080257HCID 58080257, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 6-(Boc-amino)hexylamine (4.95 g, 23 mmol) and Et3N (2 eq, 6.4 ml, 46 mmol) in 25 ml CH3CN was added dropwise 4-phenoxybenzenesulfonyl chloride solution (1 eq, 6.16 g, 23 mmol) in 15 ml CH3CN. The reaction was stirred for 2 days at room temperature. The precipitate was filtered and the solvent was evaporated. The residue was purified by silica gel chromatography [eluent: CH2Cl2/1-2% MeOH] to yield 6.68 g (64%) a colorless oil, which solidified to a white solid, m.p.=77-78° C.

Workup

  1. filtrationThe precipitate was filtered
  2. customthe solvent was evaporated
  3. customThe residue was purified by silica gel chromatography [eluent: CH2Cl2/1-2% MeOH]

Sources & evidence

ORD record
ord-5f8388f3336d409ba55ada90fd18ac76
Source dataset
uspto-grants-2015_03
Patent number
US08993544B2

Reaction notes

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