Methylamine → HCID 4369084, compound

HRID 1457303Notes

Reaction equation

HRID 1457303 reaction equation
[CH3:1][NH2:2].CO[C:5](=[O:24])[C@H:6]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[NH:7][C:8]([NH:10][C:11]1[S:12][C:13](=[S:16])[NH:14][N:15]=1)=[O:9]>C(O)C>[S:16]=[C:13]1[S:12][C:11]([NH:10][C:8]([NH:7][C@@H:6]([CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:5]([NH:2][CH3:1])=[O:24])=[O:9])=[N:15][NH:14]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 10544993HCID 10544993, compound

Product 1

HCID 4369084HCID 4369084, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A saturated solution of methylamine in ethanol (50 mL) and N-[[(4,5-dihydro-5-thioxo-1,3,4-thiadiazol-2-yl)amino]carbonyl]-L-phenylalanine methyl ester (EXAMPLE 1; 0.770 g, 2.28 mmol) is stirred at room temperature for 6 days. The solution is concentrated, diluted with water, and acidified with 1N HCl. The resultant solids are filtered and dried to give 576 mg of the amide. Recrystallization from hot EtOAc/CH2 Cl2 /MeOH gives 390 mg (51%) of the desired product as a white solid (mp 234°-236° C.).

Workup

  1. concentrationThe solution is concentrated
  2. additiondiluted with water
  3. filtrationThe resultant solids are filtered
  4. customdried

Sources & evidence

ORD record
ord-ba6add492839484799e2f1f8cc27a7ea
Source dataset
uspto-grants-1998_12
Patent number
US05847148

Reaction notes

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