Hydrochloric Acid → HCID 70632980, compound

HRID 1414181Notes

Reaction equation

HRID 1414181 reaction equation
C(OC([NH:8][CH2:9][CH2:10][C:11](O)=[O:12])=O)(C)(C)C.C(N(CC)CC)C.C(OC([Cl:28])=O)C(C)C.[C:29]([C:31]1[CH:36]=[CH:35][C:34]([C:37]2[O:50][C:40]([CH:41]=[N:42][N:43]3[CH2:49][C:47](=[O:48])[NH:46][C:44]3=[O:45])=[CH:39][CH:38]=2)=[CH:33][CH:32]=1)#[N:30].Cl>CN(C)C=O>[ClH:28].[NH2:8][CH2:9][CH2:10][C:11]([N:46]1[C:47](=[O:48])[CH2:49][N:43]([N:42]=[CH:41][C:40]2[O:50][C:37]([C:34]3[CH:33]=[CH:32][C:31]([C:29]#[N:30])=[CH:36][CH:35]=3)=[CH:38][CH:39]=2)[C:44]1=[O:45])=[O:12]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 26804HCID 26804, compoundHCID 62365Isobutyl chloroformateHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanine

Product 1

HCID 70632980HCID 70632980, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

t-Butoxycarbonyl -β-alanine (16.1 g, 0.080 mole) in dimethylformamide (200 ml) was cooled to 0°, and triethylamine (23.8 ml, 0.17 mole) was rapidly added. The solution was kept at -5° to 0° while isobutylchloroformate (11.9 ml, 0.085 mole) was added dropwise. The solution was stirred 10 minutes and then 1-{[5-(4-cyanophenyl)furfurylidene]amino}hydantoin (recrystallized and predried at 100° overnight; 23.5 g, 0.080 mole) was rapidly added. The mixture was maintained at -5° to 0° for 0.5 hr and was then stirred 1 hour without cooling. The mixture was poured into a solution of ice water (1,400 ml) and concentrated hydrochloric acid (25 ml). The resulting solid was collected and air-dried. The product was dissolved in acetonitrile, filtered, and concentrated to a solid.

Workup

  1. additionwas added dropwise
  2. temperatureThe mixture was maintained at -5° to 0° for 0.5 hr
  3. stirringwas then stirred 1 hour
  4. temperaturewithout cooling
  5. customThe resulting solid was collected
  6. customair-dried
  7. dissolutionThe product was dissolved in acetonitrile
  8. filtrationfiltered
  9. concentrationconcentrated to a solid

Sources & evidence

ORD record
ord-a1d7c8db18c64c5aa546ec0bc26d01a2
Source dataset
uspto-grants-1977_01
Patent number
US04001222

Reaction notes

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