6-Aminohexanoic Acid → 6-(tritylamino)caproic acid

HRID 399949Notes

Reaction equation

HRID 399949 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[C:10](Cl)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>ClCCl.C(N(CC)CC)C>[C:10]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 5646-Aminohexanoic AcidHCID 6456Trityl chloride

Product 1

HCID 5969746-(tritylamino)caproic acidYield 58.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

6-Aminocaproic acid (26 g, 0.2 mole) was dissolved in dichloromethane (200 mL) by the addition of triethylamine (100 mL). Trityl chloride (120 g, 0.45 mole) was added and the solution stirred for 36 hr. The resulting solution was extracted with 1N HCl and the organic layer evaporated to dryness. The residue was suspended in 2-propanol/1N NaOH (300 mL/100 mL) and refluxed for 3 hr. The solution was evaporated to a thick syrup and added to dichloromethane (500 mL). Water was added and acidified. The phases were separated, and the organic layer dried over sodium sulfate and evaporated to dryness. The residue was suspended in hot 2-propanol, cooled, and filtered to give 43.5 g (58%) of 6-(trityl-amino)caproic acid, useful as an intermediate compound.

Workup

  1. extractionThe resulting solution was extracted with 1N HCl
  2. customthe organic layer evaporated to dryness
  3. temperaturerefluxed for 3 hr
  4. customThe solution was evaporated to a thick syrup
  5. additionadded to dichloromethane (500 mL)
  6. additionWater was added
  7. customThe phases were separated
  8. dry with materialthe organic layer dried over sodium sulfate
  9. customevaporated to dryness
  10. temperaturecooled
  11. filtrationfiltered

Sources & evidence

ORD record
ord-a2ff3e27d1394cdfa3d070d4b89eec0a
Source dataset
uspto-grants-1998_10
Patent number
US05824796

Reaction notes

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