1,1'-Carbonyldiimidazole → HCID 54284901, compound

HRID 1975677Notes

Reaction equation

HRID 1975677 reaction equation
[CH3:1][C:2]([CH3:13])([O:4][C:5]([NH:7][CH2:8][CH2:9][C:10]([OH:12])=O)=[O:6])[CH3:3].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:26][CH2:27][C:28]([N:30]1[CH2:36][C:35]2[CH:37]=[CH:38][CH:39]=[CH:40][C:34]=2[O:33][C:32]2[CH:41]=[CH:42][C:43]([Cl:45])=[CH:44][C:31]1=2)=[O:29]>O1CCCC1>[Cl:45][C:43]1[CH:42]=[CH:41][C:32]2[O:33][C:34]3[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=3[CH2:36][N:30]([C:28](=[O:29])[CH2:27][NH:26][C:10](=[O:12])[CH2:9][CH2:8][NH:7][C:5](=[O:6])[O:4][C:2]([CH3:1])([CH3:3])[CH3:13])[C:31]=2[CH:44]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 1066106110-(Aminoacetyl)-8-chloro-10,11-dihydrodibenz-[b,f][1,4]oxazepine

Product 1

HCID 54284901HCID 54284901, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

To a stirred solution of N-[(1,1-dimethylethoxy)carbonyl]-β-alanine (0.72 gram) in anhydrous tetrahydrofuran (20 mL) at 5° C. under a nitrogen atmosphere was added, in portions, 1,1'-carbonyldiimidazole (0.67 gram). The reaction was stirred at 5° C. for 30 minutes, and then at room temperature for 90 minutes. To the reaction was then added 10-(aminoacetyl)-8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepine (1.00 gram), and the reaction was stirred at room temperature under a nitrogen atmosphere overnight. The reaction was partitioned between saturated aqueous sodium bicarbonate (50 mL) and chloroform (50 mL). The layers were separated, and the aqueous layer was extracted with chloroform (50 mL), and the chloroform extracts were combined, washed with 25 mL each of saturated aqueous sodium bicarbonate, water, and brine, dried over MgSO4, and evaporated in vacuo. The crude product was purified by flash chromatography through silica gel 60 (350 mL) using 3:1 ethyl acetate:hexane. The yield of the title compound was 1.23 grams (77%).

Workup

  1. waitat room temperature for 90 minutes
  2. customThe reaction was partitioned between saturated aqueous sodium bicarbonate (50 mL) and chloroform (50 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with chloroform (50 mL)
  5. washwashed with 25 mL each of saturated aqueous sodium bicarbonate, water, and brine
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo
  8. customThe crude product was purified by flash chromatography through silica gel 60 (350 mL)

Sources & evidence

ORD record
ord-4f7c78d18cba4fd3a44006d566412216
Source dataset
uspto-grants-1994_02
Patent number
US05288719

Reaction notes

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