Benzylamine → HCID 10501888, compound

HRID 1457304Notes

Reaction equation

HRID 1457304 reaction equation
CO[C:3](=[O:22])[C@H:4]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[NH:5][C:6]([NH:8][C:9]1[S:10][C:11](=[S:14])[NH:12][N:13]=1)=[O:7].[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CCOC(C)=O>[S:14]=[C:11]1[S:10][C:9]([NH:8][C:6]([NH:5][C@@H:4]([CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:3]([NH:30][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:22])=[O:7])=[N:13][NH:12]1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 10544993HCID 10544993, compound

Product 1

HCID 10501888HCID 10501888, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-[[(4,5-dihydro-5-thioxo-1,3,4-thiadiazol-2-yl)amino]carbonyl]-L-phenylalanine methyl ester (EXAMPLE 1, 200 mg, 0.591 mmol) and benzylamine (1.0 mL) is stirred for 3 days at room temperature. The mixture is diluted with EtOAc and washed several times with 10% HCl and brine. The organic layer is dried (MgSO4), filtered, and concentrated to give 214 mg of the amide. Recrystallization from hot CH2Cl2 /hexane gives 150 mg (61%) of the title compound as a white solid (mp 198°-200° C.). Occasionally this reaction is carried out in EtOH or MeOH, especially when the amine used is methylamine. The solution is concentrated (if necessary) and either triturated with ether to give a solid (and remove excess amine) or partitioned between EtOAc and dilute HCl. Purification by flash chromatography and recrystallization is usually sufficient to provide analytically pure material.

Workup

  1. washwashed several times with 10% HCl and brine
  2. dry with materialThe organic layer is dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2eb6117ff1cb4065b8421d4c6492063f
Source dataset
uspto-grants-1998_12
Patent number
US05847148

Reaction notes

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