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

HRID 1457508Notes

Reaction equation

HRID 1457508 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 acid

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 hours. 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 hours. 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 (58%) of 6-(tritylamino)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 hours
  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-93473c8e846d419e804d37c317e524e1
Source dataset
uspto-grants-1998_12
Patent number
US05849482

Reaction notes

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