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Water → (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-(bis((1-methyl-1H-imidazol-2-yl)methyl)amino)hexanoic acid

HRID 56317
Notes
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Reaction equation

HRID 56317 reaction equation
[NH:1]([C:11]([O:13][CH2:14][CH:15]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])[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>[CH:17]1[C:16]2[CH:15]([CH2:14][O:13][C:11]([NH:1][C@@H:2]([CH2:3][CH2:4][CH2:5][CH2:6][N:7]([CH2:35][C:31]3[N:30]([CH3:29])[CH:47]=[CH:49][N:32]=3)[CH2:35][C:31]3[N:30]([CH3:29])[CH:34]=[CH:33][N:32]=3)[C:8]([OH:10])=[O:9])=[O:12])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]=2[CH:20]=[CH:19][CH:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 12985318(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-(bis((1-methyl-1H-imidazol-2-yl)methyl)amino)hexanoic acid
Yield 92%

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-(((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-0cfc7421e0b44442bf0f9cbd605c1734
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09433594B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes