Water → 6-(bis((1-methyl-1H-imidazol-2-yl)methyl)amino)hexanoic acid

HRID 1043372Notes

Reaction equation

HRID 1043372 reaction equation
N(C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].Cl.[CH3:29][N:30]1[CH:34]=[CH:33][N:32]=[C:31]1[CH:35]=O.[BH-](O[C:47]([CH3:49])=O)(OC(C)=O)OC(C)=O.[Na+].O>ClCCCl>[CH3:29][N:30]1[CH:34]=[CH:33][N:32]=[C:31]1[CH2:35][N:7]([CH2:35][C:31]1[N:30]([CH3:29])[CH:47]=[CH:49][N:32]=1)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:8]([OH:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 11858928(2S)-6-amino-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)hexanoic acid hydrochloride

Product 1

HCID 674296096-(bis((1-methyl-1H-imidazol-2-yl)methyl)amino)hexanoic acidYield 160%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of Fmoc-Lys-OH.HCl (1.822 g, 4.5 mmol) and 1-methyl-1H-imidazole-2-carbaldehyde (1.10 g, 10 mmol) in DCE (50 mL) was stirred at 75° C. for 30 min under nitrogen. The reaction mixture was cooled to 0° C., and treated with NaBH(OAc)3 (3.165 g, 15 mmol). The reaction mixture was stirred at room temperature for overnight and decomposed with water. The reaction mixture was extracted with DCM, the organic layer dried and concentrated under reduced pressure. The residue was purified by flash chromatography over silica gel to afford (S)-2-4(9H-fluoren-9-yl)methoxy)carbonylamino)-6-(bis((1-methyl-1H-imidazol-2-yl)methyl)amino)hexanoic acid (2.30 g, 92%). MS (ESI), 557 (M+H)+.

Workup

  1. extractionThe reaction mixture was extracted with DCM
  2. customthe organic layer dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-822e752198f54147a815e25fff1d54e9
Source dataset
uspto-grants-2013_10
Patent number
US08562945B2

Reaction notes

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