Methylamine → HCID 178485745, compound

HRID 64827Notes

Reaction equation

HRID 64827 reaction equation
[NH:1]1[C@H:4]([C:5]([NH:7][C@H:8]([C:15]([N:17]2[CH2:24][CH2:23][CH2:22][C@H:18]2[C:19](O)=[O:20])=[O:16])[CH2:9][C:10]2[N:14]=[CH:13][NH:12][CH:11]=2)=[O:6])[CH2:3][C:2]1=[O:25].C1C=CC2N(O)N=[N:32][C:30]=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.CN>CN(C=O)C.CO>[NH:1]1[C@H:4]([C:5]([NH:7][C@H:8]([C:15]([N:17]2[CH2:24][CH2:23][CH2:22][C@H:18]2[C:19]([NH:32][CH3:30])=[O:20])=[O:16])[CH2:9][C:10]2[N:14]=[CH:13][NH:12][CH:11]=2)=[O:6])[CH2:3][C:2]1=[O:25]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 178516327HCID 178516327, compound

Product 1

HCID 178485745HCID 178485745, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

In 2 ml of DMF were dissolved 300 mg of Nα -[(S)-2-azetidinone-4-carbonyl]-L-histidyl-L-proline (13) (obtained in Example 3), 116 mg of HOBT, and 177 mg of DCC and after stirring for 7 hours at room temperature, the solution was cooled in an ice bath. Then 0.6 ml of a methanol solution of 30% methylamine was added to the solution and the mixture was reacted overnight with stirring at 2° to 6° C. Insoluble matters were filtered off and the filtrate was concentrated to dryness under reduced pressure. The residue thus formed was purified by column chromatography using LiChroprep Si 60(size B). By using chloroform-methanol-aqueous ammonia (40:10:1) as the eluant, Nα -[(S)-2-azetidinone-4-carbonyl]-L-histidyl-N-methyl-L-prolinamide (46) was obtained. The product was dissolved in water and then lyophilized. The amount of the product thus obtained was 149 mg.

Workup

  1. temperaturethe solution was cooled in an ice bath
  2. customthe mixture was reacted overnight
  3. stirringwith stirring at 2° to 6° C
  4. filtrationInsoluble matters were filtered off
  5. concentrationthe filtrate was concentrated to dryness under reduced pressure
  6. customThe residue thus formed
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-260b11f0cdc14ae29f99578e2c400c4f
Source dataset
uspto-grants-1986_09
Patent number
US04610821

Reaction notes

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