1,1'-Carbonyldiimidazole → HCID 131728696, compound

HRID 554776Notes

Reaction equation

HRID 554776 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C@@H:10]([CH2:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[O:22][CH3:23])[C:11](O)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)([N:26]1C=CN=C1)=O.O.N>O1CCCC1>[NH2:26][C:11](=[O:12])[C@H:10]([CH2:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[O:22][CH3:23])[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 12896473Azane;hydrateHCID 66934929HCID 66934929, compound

Product 1

HCID 131728696HCID 131728696, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Step 3) To (2R)-3-[(tert-butoxycarbonyl)amino]-2-(5-chloro-2-methoxybenzyl)propanoic acid (15 g) in tetrahydrofuran (75 ml) solution, 1,1′-carbonyldiimidazole (7.8 g) was added under ice cooling and the mixture was stirred at room temperature for 1 hour. The reaction solution was cooled to 0° C., 28% ammonia water (15 ml) was added, and the mixture was stirred at room temperature for 30 minutes. To the reaction solution, distilled water, ethyl acetate, and tetrahydrofuran were added, the aqueous layer and the organic layer were separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was successively washed with saturated potassium hydrogensulfate aqueous solution and saturated saline, dried over with anhydrous sodium sulfate, and concentrated until a small amount of ethyl acetate remained. Hexane was added to the concentrated solution, and the precipitated solid was collected by filtration to obtain the title compound (13.5 g).

Workup

  1. temperatureThe reaction solution was cooled to 0° C.
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. distillationTo the reaction solution, distilled water, ethyl acetate, and tetrahydrofuran
  4. additionwere added
  5. customthe aqueous layer and the organic layer were separated
  6. extractionthe aqueous layer was extracted with ethyl acetate
  7. washThe combined organic layer was successively washed with saturated potassium hydrogensulfate aqueous solution and saturated saline
  8. dry with materialdried over with anhydrous sodium sulfate
  9. concentrationconcentrated until a small amount of ethyl acetate
  10. additionHexane was added to the concentrated solution
  11. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-26b1ff3bc18a432883fbf75e3794f8bf
Source dataset
uspto-grants-2011_11
Patent number
US08049006B2

Reaction notes

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