Potassium Carbonate → Cyclopentyl(S)-2-[(4-Aminobenzyl)-tert-butoxycarbonyl amino]-4-methylpentanoate

HRID 1667362Notes

Reaction equation

HRID 1667362 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-])=O.[C:12](=[O:15])([O-])[O-:13].[K+].[K+].[CH:18]1([O:23][C:24](=[O:31])[C@H:25]([CH2:27][CH:28]([CH3:30])[CH3:29])[NH2:26])[CH2:22][CH2:21][CH2:20][CH2:19]1>CN(C=O)C.CCOC(C)=O>[NH2:1][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][N:26]([C:12]([O:13][C:7]([CH3:10])([CH3:8])[CH3:6])=[O:15])[C@@H:25]([CH2:27][CH:28]([CH3:29])[CH3:30])[C:24]([O:23][CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)=[O:31])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromideHCID 53718217(S)-cyclopentyl 2-amino-4-methylpentanoate2×

Product 1

HCID 57658375Cyclopentyl(S)-2-[(4-Aminobenzyl)-tert-butoxycarbonyl amino]-4-methylpentanoateYield 156.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Nitrobenzyl bromide (11 g, 50 mmol) was dissolved in DMF (180 ml) and potassium carbonate (13.6 g, 99 mmol) added, followed by L-leucine cyclopentyl ester (Intermediate 8) (16 g, 43 mmol). The reaction was stirred for 18 h at RT. The residue was diluted with EtOAc (500 ml) and washed with water (3×100 ml), dried (Na2SO4) filtered and concentrated to dryness to give the crude product (15.8 g) which was used in the next step without further purification. LCMS purity 60%, m/z 335 [M+H]+.

Workup

  1. washwashed with water (3×100 ml)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-e1e8bf3b6d9b4e6ea8f871bb5d406d7c
Source dataset
uspto-grants-2011_10
Patent number
US08044211B2

Reaction notes

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