Tert-butyl 5-(5-benzyloxy-5-oxo-pent-1-ynyl)imidazole-1-carboxylate → 5-(3-Tert-butoxycarbonylimidazol-4-yl)pentanoic acid

HRID 870583Notes

Reaction equation

HRID 870583 reaction equation
C([O:8][C:9](=[O:26])[CH2:10][CH2:11][C:12]#[C:13][C:14]1[N:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:17]=[N:16][CH:15]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[C:22]([O:21][C:19]([N:18]1[C:14]([CH2:13][CH2:12][CH2:11][CH2:10][C:9]([OH:26])=[O:8])=[CH:15][N:16]=[CH:17]1)=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

5

Reactant 2

HCID 86726544Tert-butyl 5-(5-benzyloxy-5-oxo-pent-1-ynyl)imidazole-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 867265455-(3-Tert-butoxycarbonylimidazol-4-yl)pentanoic acidYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Vigorously stir a 60° C. solution of tert-butyl 5-(5-benzyloxy-5-oxo-pent-1-ynyl)imidazole-1-carboxylate (0.17 g; 1.0 equiv; 0.48 mmoles) and palladium (10% on carbon; 0.030 g; 0.014 mmoles) in methanol (13 mL) under 1 atmosphere of hydrogen for 16 hours. Filter and concentrate to afford the desired 5-(3-tert-butoxycarbonylimidazol-4-yl)pentanoic acid (0.128 g; 99%) as a white solid: MS (m/z): 213(M-t-Bu+1).

Workup

  1. filtrationFilter
  2. concentrationconcentrate

Sources & evidence

ORD record
ord-9f2f64a327f84eeca5f8d2b1ab51826a
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

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