Diazopropane → HCID 86736941, compound

HRID 2049751Notes

Reaction equation

HRID 2049751 reaction equation
[SH:1][CH2:2][CH2:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH:7]1[C:13]([OH:15])=[O:14])=[O:5].[N+](=[CH:18][CH2:19][CH3:20])=[N-].[N+](NC(=N)N(N=O)CCC)([O-])=O>CCOCC>[SH:1][CH2:2][CH2:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH:7]1[C:13]([O:15][CH2:18][CH2:19][CH3:20])=[O:14])=[O:5]

Participants

5

Reactant 3

HCID 12224242DiazopropaneHCID 20344390HCID 20344390, compoundHCID 135448158N'-nitro-N-nitroso-N-propylguanidine

Product 1

HCID 86736941HCID 86736941, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred suspension of 11.6 gms. of DL-1-(3-mercapto-1-oxopropyl)-4-methylpiperazine-2-carboxylic acid in 150 ml. of ether there is added dropwise a solution of diazopropane in ether [prepared from 8.75 g. of N'-nitro-N-nitroso-N-propylguanidine by the procedure of McKay et al. Can. J. Res. 28 B, 683(1950)]. The mixture is stirred for an additional three hours, filtered and washed twice with 100 ml. of 5% aqueous sodium bicarbonate solution. The ether solution is dried over anhydrous magnesium sulfate, and then concentrated under atmospheric pressure, leaving as a residue the desired DL-1-(3-mercapto-1-oxopropyl)-4-methylpiperazine-2-carboxylic acid, n-propyl ester.

Workup

  1. additionTo a stirred suspension of 11.6 gms
  2. customprepared from 8.75 g
  3. filtrationfiltered
  4. washwashed twice with 100 ml
  5. dry with materialThe ether solution is dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under atmospheric pressure

Sources & evidence

ORD record
ord-12d44ec0b9734b7595c32c080cc07346
Source dataset
uspto-grants-1980_04
Patent number
US04198509

Reaction notes

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