6-Aminohexanoic Acid → 6-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)hexanoic acid

HRID 279727Notes

Reaction equation

HRID 279727 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[CH:10]1[C:22]2[CH:21]([CH2:23][O:24][C:25](ON3C(=O)CCC3=O)=[O:26])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[CH:13]=[CH:12][CH:11]=1>C([O-])([O-])=O.[Na+].[Na+].CN(C=O)C.O>[CH:10]1[C:22]2[CH:21]([CH2:23][O:24][C:25]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])=[O:26])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 2

HCID 5646-Aminohexanoic AcidHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimide

Product 1

HCID 27560876-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)hexanoic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 10340Sodium CarbonateSolvent

Procedure

To a solution (“soln.”) of 6-aminohexanoic acid (1; 144 mg, 1.1 mmol) in 9% aq. Na2CO3 soln. (2.4 ml) was added a soln. of (9H-fluoren-9-yl)methyl succinimidyl carbonate (2; 337 mg, 1 mmol) in DMF (2.5 ml). After stirring for 1 h at room temperature (“r.t.”), the mixture was diluted with H2O (50 ml) and extracted twice with Et2O (2×20 ml). Then, the H2O phase was acified with conc. HCl soln. to pH 2 and extracted with AcOEt (5×30 ml). The organic (“org.”) layer was dried (MgSO4) and evaporated. The residue was crystallized in CHCl3/petroleum ether: 306 mg (86%) of 3. Colorless crystals. M.p. 116°. 1H-NMR (CDCl3): 7.80-7.55 (2m, H—C(1)(fmoc), H—C(4)(fmoc), H—C(5)fmoc, H—C(8)(fmoc); 7.45-7.25 (m, H—C(2)(fmoc), H—C(3)(fmoc), H—C(6)(fmoc), H—C(7)(fmoc); 4.45 (m, CH2O)(fmoc)); 4.2(m, H—C(9)(fmoc)); 3.25-3.0, 2.4, 1.8-1.3 (3m, NH(CH2)5CO). Anal. calc. for C21H23NO4 (353.42): C 71.37, H 6.56, N 3.96; found: C 71.35, H 6.65, N 3.93.

Workup

  1. addition(2.4 ml) was added a soln
  2. extractionextracted twice with Et2O (2×20 ml)
  3. extractionto pH 2 and extracted with AcOEt (5×30 ml)
  4. dry with materialThe organic (“org.”) layer was dried (MgSO4)
  5. customevaporated
  6. customThe residue was crystallized in CHCl3/petroleum ether

Sources & evidence

ORD record
ord-f0285af626fd45b38d7dec6a447fb19e
Source dataset
uspto-grants-2002_03
Patent number
US06362171B1

Reaction notes

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