6-Aminohexanoic Acid → 6-Aminocaproic acid N'-fmoc hydrazide

HRID 260499Notes

Reaction equation

HRID 260499 reaction equation
[CH2:1]([CH2:7][CH2:8][NH2:9])[CH2:2][CH2:3][C:4]([OH:6])=O.[C:10]([O:14][CH2:15][CH:16]1[C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)(=[O:13])[NH:11][NH2:12]>>[C:10]([NH:11][NH:12][C:4](=[O:6])[CH2:3][CH2:2][CH2:1][CH2:7][CH2:8][NH2:9])([O:14][CH2:15][CH:16]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13]

Participants

3

Reactant 2

HCID 5646-Aminohexanoic AcidHCID 1618839-Fluorenylmethyl carbazate

Product 1

HCID 587949346-Aminocaproic acid N'-fmoc hydrazide

Procedure

Using anhydrous conditions and under a nitrogen gas blanket, a 200 ml round bottom flask was charged with 4.90 g (10.48 mmol) of N-BOC-6-aminocaproate (N-(FMOC) hydrazide), and 10 ml of methylene chloride. The reaction mixture was then stirred at room temperature as 16 ml of trifluoroacetic acid (Schweizerhall) dissolved in 16 ml of methylene chloride was slowly added. The resultant homogeneous solution was allowed to stir for an additional 2 h and then 15 ml of toluene was added. The solvents and any remaining trifluoroacetic acid were then distilled off under reduced pressure. The distillation residue was twice more azeotroped with 15 ml portions of toluene to leave 8.49 g of orange oil. 1H NMR showed this crude material to contain the peaks associated with aminocaproic acid and a FMOC substituent. However, no tert-butyl peak was observed between 1-2 ppm showing removal of the BOC protecting group. This product was used without further purification.

Workup

  1. customremoval of the BOC protecting group
  2. customThis product was used without further purification

Sources & evidence

ORD record
ord-79b76aaa21b1428eb4c0dcf2dfaf8eb9
Source dataset
uspto-grants-1996_06
Patent number
US05527885

Reaction notes

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