Methanol → HCID 10543975, compound

HRID 1457305Notes

Reaction equation

HRID 1457305 reaction equation
C[O:2][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].CO.[OH-].[K+]>O>[S:14]=[C:11]1[S:10][C:9]([NH:8][C:6]([NH:5][C@H:4]([C:3]([OH:22])=[O:2])[CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:7])=[N:13][NH:12]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 10544993HCID 10544993, compound

Product 1

HCID 10543975HCID 10543975, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-[[(4,5-dihydro-5-thioxo-1,3,4-thiadiazol-2-yl)amino]carbonyl]-L-phenylalanine methyl ester (EXAMPLE 1; 528 mg, 1.56 mmol), MeOH (20 mL), H2O (5.0 mL) and KOH (350 mg, 6.24 mmol) is stirred at room temperature for 16 hours. The solution is concentrated (to remove the MeOH), acidified with 10% HCl, and extracted with EtOAc (3×20 mL). The organic layers are dried (MgSO4), filtered, and concentrated to give 490 mg (97%) of the title compound (mp 130° C.).

Workup

  1. concentrationThe solution is concentrated (
  2. customto remove the MeOH),
  3. extractionextracted with EtOAc (3×20 mL)
  4. dry with materialThe organic layers are dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-aa8a5821607b49478782623e78479a86
Source dataset
uspto-grants-1998_12
Patent number
US05847148

Reaction notes

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