Triethylamine → HCID 12686579, compound

HRID 452367Notes

Reaction equation

HRID 452367 reaction equation
C(N(CC)CC)C.[CH2:8]([O:15][C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.ClC(OCC)=O.O[N:34]1[C:38](=[O:39])[CH2:37][CH2:36][C:35]1=[O:40]>CN(C)C=O>[CH2:8]([O:15][C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][N:34]1[C:38](=[O:39])[CH2:37][CH2:36][C:35]1=[O:40])=[O:25])=[O:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 747586-(((Phenylmethoxy)carbonyl)amino)hexanoic acidHCID 80170N-Hydroxysuccinimide

Product 1

HCID 12686579HCID 12686579, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (0.63 ml, 4.52 mmol) is added to a solution of 6-(benzyloxycarbonylamino)hexanoic acid (1.00 g, 3.77 mmol) in dimethylformamide (20 ml) and the mixture is left to stir at ambient temperature and under argon for 30 minutes. The solution is cooled to 0° C. and ethyl chloroformate (0.43 ml, 4.52 mmol) is added dropwise. After two hours at ambient temperature, N-hydroxysuccinimide (0.52 g, 4.52 mmol) is added and the mixture is left to stir overnight at ambient temperature. The mixture is evaporated to dryness before taking up the residue in water to which ethyl acetate is added. The phases are separated and the aqueous phase is extracted with ethyl acetate. The organic phases are combined, dried over sodium sulfate, filtered and evaporated to dryness before purification on a silica gel column with an ethyl acetate/pentane mixture (75/25 v/v) as eluent. The fractions, once evaporated, give 1.13 g of succinimidyl 6(benzyloxycarbonylamino)hexanoate in the form of an oil.

Workup

  1. waitthe mixture is left
  2. temperatureThe solution is cooled to 0° C.
  3. waitAfter two hours at ambient temperature
  4. waitthe mixture is left
  5. stirringto stir overnight at ambient temperature
  6. customThe mixture is evaporated to dryness
  7. additionis added
  8. customThe phases are separated
  9. extractionthe aqueous phase is extracted with ethyl acetate
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. customevaporated to dryness before purification on a silica gel column with an ethyl acetate/pentane mixture (75/25 v/v) as eluent
  13. customThe fractions, once evaporated

Sources & evidence

ORD record
ord-b56ca78aef7541079ab63fcc5c021f81
Source dataset
uspto-grants-2013_07
Patent number
US08492352B2

Reaction notes

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