1,1'-Carbonyldiimidazole → HCID 57978296, compound

HRID 1866541Notes

Reaction equation

HRID 1866541 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:27]1[CH:31]=[CH:30]N=C1)(N1C=CN=C1)=O.[CH:32](N(CC)C(C)C)(C)[CH3:33]>ClCCl>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]([NH:27][CH2:31][CH2:30][CH2:32][CH3:33])=[O:17])=[CH:18][CH:19]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 166409054-(2-{[(Tert-butoxy)carbonyl]amino}ethyl)benzoic acid

Product 1

HCID 57978296HCID 57978296, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-{2-[(tert-butoxycarbonyl)amino]ethyl}benzoic acid (22.2 g, 83.6 mmol) (EP0836839, p60) carbonyldiimidazole (21.36 g, 131.7 mmol), and N,N-diisopropylethylamine (20 mL, 115.1 mmol) in dichloromethane (600 mL) was stirred at room temperature for 2 hours. nButylamine (10 mL, 101.18 mmol) was then added and the mixture was stirred for a further 18 hours at room temperature. The reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate and washed with 10% citric acid (2×50 mL), saturated sodium hydrogen carbonate solution (200 mL), water (200 mL) and brine (200 mL). The organic solution was dried over sodium sulfate and concentrated in vacuo to give a cream powder. The powder was purified by column chromatography on silica gel, eluting with dichloromethane:methanol, 99:1, to afford the title compound (17.5 g, 65%). LRMS Cl m/z 383.3 [M+NH4]+, m.p.=118° C.

Workup

  1. additionnButylamine (10 mL, 101.18 mmol) was then added
  2. stirringthe mixture was stirred for a further 18 hours at room temperature
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed with 10% citric acid (2×50 mL), saturated sodium hydrogen carbonate solution (200 mL), water (200 mL) and brine (200 mL)
  6. dry with materialThe organic solution was dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto give a cream powder
  9. customThe powder was purified by column chromatography on silica gel
  10. washeluting with dichloromethane

Sources & evidence

ORD record
ord-4c5a77a8ae084c4db72fce8cbd89c933
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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