Hydrogen Sulfide → methyl [[1-[N-[p-(thiocarbamoyl)benzoyl]-glycyl]-4-piperidinyl]oxy]acetate

HRID 1768724Notes

Reaction equation

HRID 1768724 reaction equation
[C:1]([C:3]1[CH:26]=[CH:25][C:6]([C:7]([NH:9][CH2:10][C:11]([N:13]2[CH2:18][CH2:17][CH:16]([O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH2:15][CH2:14]2)=[O:12])=[O:8])=[CH:5][CH:4]=1)#[N:2].[SH2:27]>N1C=CC=CC=1.C(N(CC)CC)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][CH2:10][C:11]([N:13]2[CH2:14][CH2:15][CH:16]([O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH2:17][CH2:18]2)=[O:12])=[O:8])=[CH:25][CH:26]=1)(=[S:27])[NH2:2]

Participants

4

Reactant 2

HCID 402Hydrogen SulfideHCID 57145608methyl [[1-[N-(p-cyanbenzoyl)glycyl]-4-piperidinyl]oxy]acetate

Product 1

HCID 53924674methyl [[1-[N-[p-(thiocarbamoyl)benzoyl]-glycyl]-4-piperidinyl]oxy]acetate

Reagents, catalysts & solvents 1

HCID 22561186Pyridine triethylamineSolvent

Procedure

A solution of 1.5 g of methyl [[1-[N-(p-cyanbenzoyl)glycyl]-4-piperidinyl]oxy]acetate in 215 ml of pyridine/triethylamine 40:3 is saturated with hydrogen sulphide and left at room temperature for 24 hours. After removing the solvent, the residue is taken up in ethyl acetate and washed with saturated sodium chloride solution. The organic extracts are dried and concentrated. After chromatography of the residue on silica gel with ethyl acetate followed by ethyl acetate/methanol, there are isolated 1.34 g of methyl [[1-[N-[p-(thiocarbamoyl)benzoyl]-glycyl]-4-piperidinyl]oxy]acetate, MS (FAB): 394 (M+H)+.

Workup

  1. customAfter removing the solvent
  2. washwashed with saturated sodium chloride solution
  3. customThe organic extracts are dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c5981bc11df044c2b1a8b5d5d5c913de
Source dataset
uspto-grants-1995_01
Patent number
US05378712

Reaction notes

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